TITLE

2-(PHENYLOXY OR PHENYLTHIO)PYRIMIDINE DERIVATIVES AS HERBICIDES

FIELD OF THE INVENTION

This invention relates to certain pyrimidinyloxy benzene derivatives, their N-oxides, salts and compositions, and methods of their use for controlling undesirable vegetation.

BACKGROUND OF THE INVENTION

The control of undesired vegetation is extremely important in achieving high crop efficiency. Achievement of selective control of the growth of weeds especially in such useful crops as rice, soybean, sugar beet, maize, potato, wheat, barley, tomato and plantation crops, among others, is very desirable. Unchecked weed growth in such useful crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. The control of undesired vegetation in noncrop areas is also important. Many products are commercially available for these purposes, but the need continues for new compounds that are more effective, less costly, less toxic, environmentally safer or have different sites of action.

SUMMARY OF THE INVENTION

This invention is directed to compounds of Formula 1 (including all all geometric and stereoisomers), N-oxides, and salts thereof, agricultural compositions containing them and their use as herbicides:

wherein

A is;

A-l A-2 A-3 A-4 A-5 A-6 A-7

B is O or S; R ¹ is H, C _Y -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C _Y -C ₆ haloalkyl, C ₂ -C ₆ haloalkenyl, C ₂ -Cg haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C3-C6 halocycloalkylalkyl, C ₄ -Cg alkylcycloalkyl, C ₄ -Cg cycloalkylalkyl, C^-Cg alkylamino, Ci-Cg haloalkylamino, C ₂ -CI Q dialkylamino, C ₂ -CI Q halodialkylamino, C3-C6 cycloamino, Ci-Cg alkoxy, C3-C6 alkenyloxy, C3-C6 alkynyloxy, Ci-Cg haloalkoxy, C3-C6 haloalkenyloxy, C3-C6 haloalkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C ₄ -Cg cycloalkylalkoxy, C ₄ -Cg halocycloalkylalkoxy, C ₂ -Cg alkoxyalkyl, C ₂ -Cg haloalkoxyalkyl, C ₂ -Cg alkoxyhaloalkyl, C ₂ -Cg alkoxyalkoxy, C ₂ -Cg cyanoalkyl, C ₂ -Cg cyanoalkoxy, C3-C7 cyanoalkoxyalkyl, Ci-Cg hydroxyalkyl, Ci-Cg nitroalkyl, Ci-Cg alkylthio, Ci-Cg haloalkylthio, C3-C8 cycloalkylthio, Ci-Cg alkenylthio, Ci-Cg alkylsulfinyl, Ci-Cg haloalkylsulfinyl, Ci-Cg alkylsulfonyl, Ci-Cg

haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C ₂ -Cg alkylthioalkyl, C ₂ -Cg haloalkylthioalkyl, benzyl, -N(R ⁷ )(OR ⁸ ), -ON(R ^9a )(R ^9b ) or -N(R ⁷ )N(R ^9a )(R ^9b );

Z is O or S;

R ² is halogen, cyano, nitro, Ci-Cg alkoxy, Ci-Cg alkyl, C ₂ -Cg alkenyl, C ₂ -Cg

alkynyl, Ci~C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl or -SO _n R ¹⁰ ;

each R ³ is independently halogen, cyano, nitro, CHO, C(=0) H ₂ , C(=S) H ₂ ,

S0 ₂ H ₂ , C!-C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ alkynyl, C1-C4 haloalkyl, C ₂ -C ₄ haloalkenyl, C ₂ -C ₄ haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C ₄ -Cg alkylcycloalkyl, C ₄ -Cg cycloalkylalkyl, C ₂ -Cg alkylcarbonyl, C ₂ -Cg haloalkylcarbonyl, C ₂ -Cg alkoxycarbonyl, C3-C7 cycloalkylcarbonyl, C ₂ -C ₄ alkoxy, C3~C ₄ alkenyloxy, C3~C ₄ alkynyloxy, Ci-C ₄ haloalkoxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C ₄ -Cg cycloalkylalkoxy, C ₂ -Cg alkoxyalkyl, C ₂ -Cg haloalkoxyalkyl, C ₂ -Cg alkoxyhaloalkyl, C ₂ -Cg

alkoxyalkoxy, C ₂ -C ₄ alkylcarbonyloxy, C ₂ -Cg cyanoalkyl, C ₂ -Cg cyanoalkoxy, C ₂ -C ₄ alkylthioalkyl, -C(=0)N(R ^{l la} )(R ^{l lb} ), -C(=NOR ¹² )H, -C(=N(R ¹³ ))H or

-SO _n Rl4;

m is 0, 1, 2 or 3;

each n is independently 0, 1 or 2;

R ⁴ is H, C _x -C ₆ alkyl or C _x -C ₆ haloalkyl;

R ⁵ is H, C _x -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C _x -C ₆ haloalkyl, C ₂ -C ₆

haloalkenyl, C ₂ -Cg haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C ₄ -Cg alkylcycloalkyl, C ₄ -Cg cycloalkylalkyl, C ₂ -Cg alkoxyalkyl, C ₂ -Cg haloalkoxyalkyl, C ₂ -Cg alkoxyhaloalkyl, C ₂ -Cg cyanoalkyl, C3-C7

cyanoalkoxyalkyl, Ci-Cg hydroxyalkyl, Ci-Cg nitroalkyl, C ₂ -Cg alkylthioalkyl, C ₂ -Cg haloalkylthioalkyl or benzyl;

each R ^6a and R ^6b is independently H, C _x -C ₆ alkyl or C _x -C ₆ haloalkyl; R ⁷ is H, C _x -C ₆ alkyl or C _x -C ₆ haloalkyl;

R ⁸ is H, Ci-Cg alkyl, Ci-Cg haloalkyl, C2-Cg alkoxyalkyl, C2-Cg haloalkoxyalkyl or

C2-Cg cyanoalkyl;

each R ^9a and R ^9b is independently H, Ci-Cg alkyl or Ci-Cg haloalkyl;

R ¹⁰ is independently Ci-Cg alkyl, Ci-Cg haloalkyl, Ci-Cg alkylamino or C2-C ₁ 0 dialkylamino;

each R ^{l la} is independently C ₁ -C4 alkyl or C ₁ -C4 haloalkyl;

each R ^{l lb} is independently H, C ₁ -C4 alkyl or C ₁ -C4 haloalkyl;

each R ¹² is independently H or C ₁ -C4 alkyl;

each R ¹³ is independently H, amino, C ₁ -C4 alkyl or C ₁ -C4 alkylamino;

each R ¹⁴ is independently Ci-Cg alkyl, Ci-Cg haloalkyl, Ci-Cg alkylamino or

C2-C ₁ 0 dialkylamino; and

R ¹⁵ is H or Ci-C ₆ alkyl;

provided that

(i) when A is A-l then R ¹ is other than H, Ci-Cg alkyl or C2-Cg alkenyl;

(ii) when A is A-6, then R ¹ is other than Ci-Cg alkyl sulfonyl;

(iii) when A is A-l, R ² is CI and R ³ is 3-Br, then R ¹ is other than C2 alkylthio, C2 alkyl sulfinyl or C2 alkyl sulfonyl; and

(iv) the compound of Formula 1 is other than methyl 2-[(5-chloro-2- pyrimidinyl)oxy]benzoate (CAS Registry No. 854215-38-6), methyl 2-[(5- bromo-2-pyrimidinyl)oxy]benzoate (CAS Registry No. 1086397-52-5), l-[2-[(5- bromo-2-pyrimidinyl)oxy]phenyl]-ethanone (CAS Registry No. 1147704-06-0) and 2-[(5-bromo-2-pyrimidinyl)oxy]-benzeneacetonitrile (CAS Registry No. 138193-83-6).

More particularly, this invention pertains to a compound of Formula 1 (including all stereoisomers), an N-oxide or a salt thereof. This invention also relates to a herbicidal composition comprising a compound of the invention (i.e. in a herbicidally effective amount) and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents. This invention further relates to a method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with a herbicidally effective amount of a compound of the invention (e.g., as a composition described herein).

This invention also includes a herbicidal mixture comprising (a) a compound selected from Formula 1, N-oxides, and salts thereof, and (b) at least one additional active ingredient selected from (bl) through (bl6); and salts of compounds of (bl) through (bl6), as described below. DETAILS OF THE INVENTION

As used herein, the terms "comprises," "comprising," "includes," "including," "has," "having," "contains", "containing," "characterized by" or any other variation thereof, are intended to cover a non-exclusive inclusion, subject to any limitation explicitly indicated. For example, a composition, mixture, process or method that comprises 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, mixture, process or method.

The transitional phrase "consisting of excludes any element, step, or ingredient not specified. If in the claim, such would close the claim to the inclusion of materials other than those recited except for impurities ordinarily associated therewith. When the phrase "consisting of appears in a clause of the body of a claim, rather than immediately following the preamble, it limits only the element set forth in that clause; other elements are not excluded from the claim as a whole.

The transitional phrase "consisting essentially of is used to define a composition or method that includes materials, steps, features, components, or elements, in addition to those literally disclosed, provided that these additional materials, steps, features, components, or elements do not materially affect the basic and novel characteristic(s) of the claimed invention. The term "consisting essentially of occupies a middle ground between "comprising" and "consisting of.

Where applicants have defined an invention or a portion thereof with an open-ended term such as "comprising," it should be readily understood that (unless otherwise stated) the description should be interpreted to also describe such an invention using the terms "consisting essentially of or "consisting of."

Further, unless expressly stated to the contrary, "or" refers to an inclusive or and not to an exclusive or. For example, a condition A or B is satisfied by any one 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 "an" preceding an element or component of the invention are intended to be nonrestrictive regarding the number of instances (i.e. occurrences) of the element or component. Therefore "a" or "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 meant to be singular.

As referred to herein, the term "seedling", used either alone or in a combination of words means a young plant developing from the embryo of a seed.

As referred to herein, the term "broadleaf used either alone or in words such as

"broadleaf weed" means dicot or dicotyledon, a term used to describe a group of angiosperms characterized by embryos having two cotyledons. In the above recitations, the term "alkyl", used either alone or in compound words such as "alkylthio" or "haloalkyl" includes straight-chain or branched alkyl, such as, methyl, ethyl, ^-propyl, / ^' -propyl, or the different butyl, pentyl or hexyl isomers. "Alkenyl" includes straight-chain or branched alkenes such as ethenyl, 1-propenyl, 2-propenyl, and the different butenyl, pentenyl and hexenyl isomers. "Alkenyl" also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. "Alkynyl" includes straight-chain or branched alkynes such as ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers. "Alkynyl" can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl.

"Alkoxy" includes, for example, methoxy, ethoxy, «-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers. "Alkoxyalkyl" denotes alkoxy substitution on alkyl. Examples of "alkoxyalkyl" include CH ₃ OCH ₂ , CH ₃ OCH ₂ CH ₂ , CH ₃ CH ₂ OCH ₂ , CH ₃ CH ₂ CH ₂ CH ₂ OCH ₂ and CH ₃ CH ₂ OCH ₂ CH ₂ . "Alkoxyalkoxy" denotes alkoxy substitution on alkoxy. Examples of "alkoxyalkoxy" include CH ₃ OCH ₂ 0, (CH ₃ ) ₂ CHOCH ₂ 0, CH ₃ OCH ₂ CH ₂ 0 and CH ₃ CH ₂ OCH ₂ CH ₂ CH ₂ 0. "Alkenyloxy" includes straight-chain or branched alkenyloxy moieties. Examples of "alkenyloxy" include H ₂ C=CHCH ₂ 0, (CH ₃ ) ₂ C=CHCH ₂ 0, (CH ₃ )CH=CHCH ₂ 0, (CH ₃ )CH=C(CH ₃ )CH ₂ 0 and CH ₂ =CHCH ₂ CH ₂ 0. "Alkynyloxy" includes straight-chain or branched alkynyloxy moieties. Examples of "alkynyloxy" include HC≡CCH ₂ 0, CH ₃ C≡CCH ₂ 0 and CH ₃ C≡CCH ₂ CH ₂ 0. "Alkylthio" includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers. "Alkyl sulfinyl" includes both enantiomers of an alkylsulfinyl group. Examples of "alkylsulfinyl" include CH ₃ S(0)-, CH ₃ CH ₂ S(0)-, CH ₃ CH ₂ CH ₂ S(0)-, (CH ₃ ) ₂ CHS(0)- and the different butyl sulfinyl, pentyl sulfinyl and hexylsulfinyl isomers. Examples of " alkyl sulfonyl" include CH ₃ S(0) ₂ -, CH ₃ CH ₂ S(0) ₂ -, CH ₃ CH ₂ CH ₂ S(0) ₂ -, (CH ₃ ) ₂ CHS(0) ₂ -, and the different butyl sulfonyl, pentyl sulfonyl and hexylsulfonyl isomers. "Alkylthioalkyl" denotes alkylthio substitution on alkyl. Examples of "alkylthioalkyl" include CH ₃ SCH ₂ , CH ₃ SCH ₂ CH ₂ , CH ₃ CH ₂ SCH ₂ , CH ₃ CH ₂ CH ₂ CH ₂ SCH ₂ and CH ₃ CH ₂ SCH ₂ CH ₂ . "Cyanoalkyl" denotes an alkyl group substituted with one cyano group. "Cyanoalkoxy" denotes an alkoxy group substituted with one cyano group. "Cyanoalkoxyalkyl" denotes an alkoxyalkyl group substituted with one cyano group. Examples of "cyanoalkyl" include NCCH ₂ , NCCH ₂ CH ₂ and CH ₃ CH(CN)CH ₂ . The term "hydroxyalkyl" denotes an alkyl group substituted with one hydroxy group. Examples of "hydroxyoalkyl" include HOCH ₂ -, HOCH ₂ CH ₂ - and CH ₃ CH(OH)CH ₂ -. The term "nitroalkyl" denotes an alkyl group substituted with one nitro group. Examples of "nitroalkyl" include 0 ₂ NCH ₂ -, 0 ₂ NCH ₂ CH ₂ - and CH ₃ CH(N0 ₂ )CH ₂ -. "Alkylamino", "dialkylamino", "alkenylthio", "alkenylsulfinyl", "alkenylsulfonyl", "alkynylthio", "alkynylsulfinyl", "alkynylsulfonyl", and the like, are defined analogously to the above examples.

"Cycloalkyl" includes, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. The term "alkylcycloalkyl" denotes alkyl substitution on a cycloalkyl moiety and includes, for example, ethylcyclopropyl, z-propylcyclobutyl, 3-methylcyclopentyl and 4-methylcyclohexyl. The term "cycloalkylalkyl" denotes cycloalkyl substitution on an alkyl moiety. Examples of "cycloalkylalkyl" include cyclopropylmethyl, cyclopentylethyl, and other cycloalkyl moieties bonded to straight-chain or branched alkyl groups. The term "cycloalkylalkoxy" denotes cycloalkyl substitution on an alkoxy moiety. The term "cycloalkylcarbonyl" denotes cycloalkyl substitution bonded through a carbonyl moiety. Examples of "cycloalkylcarbonyl" include c-Pr(C=0)-, cyclopentyl(C=0)-. The term "cycloalkylsulfonyl" denotes cycloalkyl substitution bonded through a sulfonyl moiety. Examples of "cycloalkylsulfonyl" include c-Pr(S=02)-, cyclopentyl(S=02)-. The term "cycloalkylthio" denotes cycloalkyl substitution bonded through a sulfer atom. Examples of "cycloalkylthio" include c-Pr(S)-, cyclopenty(S)-. Examples of "cycloalkylalkoxy" include cyclopropylmethoxy, cyclopentylethoxy. The term "cycloalkoxy" denotes cycloalkyl linked through an oxygen atom such as cyclopentyloxy and cyclohexyloxy. The term "cycloamino" denotes a cyclic amine moiety bonded through nitrogen. Examples of "cycloamino" include -N[CH ₂ CH ₂ CH ₂ } (i.e. azetidine) and -N[CH ₂ CH ₂ CH ₂ CH ₂ }, (i.e. pyrrolidine).

The term "halogen", either alone or in compound words such as "haloalkyl", or when used in descriptions such as "alkyl substituted with halogen" includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as "haloalkyl", or when used in descriptions such as "alkyl substituted with halogen" said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of "haloalkyl" or "alkyl substituted with halogen" include F ₃ C, C1CH ₂ , CF ₃ CH ₂ and CF ₃ CC1 ₂ . The terms "halocycloalkyl", "haloalkoxy", "haloalkylthio", "haloalkylsulfinyl", "haloalkylsulfonyl", "haloalkenyl", "haloalkynyl", "haloalkoxyalkoxy", "alkoxyhaloalkyl" and the like, are defined analogously to the term "haloalkyl". Examples of halocycloalkyl include c-Pr(2-Cl), c-Bu(2,2-di-Br) and c-Hex(3,5-di-Cl). Examples of "haloalkoxy" include CF ₃ 0-, CC1 ₃ CH ₂ 0-, HCF ₂ CH ₂ CH ₂ 0- and CF ₃ CH ₂ 0-. Examples of "haloalkylthio" include CC1 ₃ S-, CF ₃ S-, CC1 ₃ CH ₂ S- and C1CH ₂ CH ₂ CH ₂ S-. Examples of "haloalkylsulfinyl" include CF ₃ S(0)-, CC1 ₃ S(0)-, CF ₃ CH ₂ S(0)- and CF ₃ CF ₂ S(0)-. Examples of "haloalkylsulfonyl" include CF ₃ S(0) ₂ -, CC1 ₃ S(0) ₂ -, CF ₃ CH ₂ S(0) ₂ - and CF ₃ CF ₂ S(0) ₂ -. Examples of "haloalkenyl" include (C1) ₂ C=CHCH ₂ - and CF ₃ CH ₂ CH=CHCH ₂ -. Examples of "haloalkynyl" include HC≡CCHC1-, CF ₃ C≡C-, CC1 ₃ C≡C- and FCH ₂ C≡CCH ₂ -. Examples of "haloalkoxyalkoxy" include CF ₃ OCH ₂ 0-, C1CH ₂ CH ₂ 0CH ₂ CH ₂ 0-, Cl ₃ CCH ₂ OCH ₂ 0- as well as branched alkyl derivatives. Examples of "alkoxyhaloalkyl" include CH ₃ OCF ₂ CH ₂ -, CH ₃ CH ₂ 0CH ₂ CC1 ₂ -, CF ₃ CH ₂ CH ₂ OCH ₂ - as well as branched alkyl derivatives.

The term "haloalkenyloxy" refers to a haloalkenyl group bonded through oxygen. Examples of "haloalkenyloxy" include (C1) ₂ C=CHCH ₂ 0- and CF ₃ CH ₂ CH=CHCH ₂ 0-. The term "haloalkylamino" refers to a haloalkyl group bonded through a nitrogen atom (i.e. as a secondary amine). Examples of "haloalkylamino" include CF ₃ H-, CC1 ₃ CH ₂ NH-, HCF ₂ CH ₂ CH ₂ H- and CF ₃ CH ₂ H-. The term "haloalkylcarbonyl" refers to a haloalkyl group bonded through a carbonyl moiety. Examples of "haloalkylcarbonyl" include CH ₂ C1C(=0)-, CH ₃ CHC1CH ₂ C(=0)- and (CH ₃ ) ₂ CC1(=0)-. The term "haloalkylthioalkyl" refers to a haloalkylthio group bonded through an alkyl moiety. Examples of "haloalkylthioalkyl" include CC1 ₃ SCH ₂ -, CF ₃ SCH ₂ -, CC1 ₃ CH ₂ SCH ₂ - and C1CH ₂ CH ₂ CH2SCH ₂ -. The term "haloalkynyloxy" refers to a haloalkynyl group bonded through an oxygen atom. Examples of "haloalkynyloxy" include HC≡CCHC10-, CF ₃ C≡CO-, CCl ₃ C≡CO- and FCH ₂ C≡CCH ₂ 0- haloalkynyloxy. The term "haloalkoxyalkyl" refers to a haloalkoxy group bonded through an alkyl moiety. Examples of "haloalkoxyalkyl" include CF ₃ OCH ₂ -, C1CH ₂ CH ₂ 0CH ₂ CH ₂ -, Cl ₃ CCH ₂ OCH ₂ - as well as branched alkyl derivatives. The term "halocycloalkoxy" refers to a halocycloalkyl group bonded through an oxygenatom. Examples of "halocycloalkoxy" include c-Pr(2-Cl) CH ₂ 0- and c-Bu(l-Cl) CH ₂ CH ₂ 0-. The term "halodialkylamino" indicate two haloalkyl groups bonded through nitrogen. Examples of "halodialkylamino" include (CH ₂ C1) ₂ N-, (CH ₂ CH ₂ C1) ₂ N- and (CH ₂ CH ₂ Cl)(CH ₂ Br)N-.

"Alkylcarbonyl" denotes a straight-chain or branched alkyl moieties bonded to a C(=0) moiety. Examples of "alkylcarbonyl" include CH ₃ C(=0)-, CH ₃ CH ₂ CH ₂ C(=0)- and (CH ₃ ) ₂ CHC(=0)-. Examples of "alkoxy carbonyl" include CH ₃ OC(=0)-, CH ₃ CH ₂ OC(=0)-, CH ₃ CH ₂ CH ₂ OC(=0)-, (CH ₃ ) ₂ CHOC(=0)- and the different butoxy- or pentoxycarbonyl isomers. Examples of "alkylcarbonyloxy" incude CH ₃ C(=0)0-, CH ₃ CH ₂ CH ₂ C(=0)0- and (CH ₃ ) ₂ CHC(=0)0-

The total number of carbon atoms in a substituent group is indicated by the "Cj-Cj" prefix where i and j are numbers from 1 to 10. For example, C 1 -C4 alkylsulfonyl designates methyl sulfonyl through butyl sulfonyl; C ₂ alkoxyalkyl designates CH ₃ OCH ₂ -; C ₃ alkoxyalkyl designates, for example, CH ₃ CH(OCH ₃ )-, CH ₃ OCH ₂ CH ₂ - or CH ₃ CH ₂ OCH ₂ -; and C4 alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH ₃ CH ₂ CH ₂ OCH ₂ - and CH ₃ CH ₂ OCH ₂ CH ₂ -.

When a compound is substituted with a substituent bearing a subscript that indicates the number of said substituents can exceed 1, said substituents (when they exceed 1) are independently selected from the group of defined substituents, e.g., (R ) _m , where m is 0, 1, 2 or 3). Further, when the subscript indicates a range, e.g. (R)i_j, then the number of substituents may be selected from the integers between i and j inclusive. When a group contains a substituent which can be hydrogen, for example (R ¹ or R ⁴ ), then when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted. When a variable group is shown to be optionally attached to a position, for example (R ) _m wherein m may be 0, then hydrogen may be at the position even if not recited in the variable group definition. When one or more positions on a group are said to be "not substituted" or "unsubstituted", then hydrogen atoms are attached to take up any free valency.

Unless otherwise indicated, a "ring" or "ring system" as a component of Formula 1 is carbocyclic or heterocyclic. The term "ring system" denotes two or more fused rings. The term "ring member" refers to an atom or other moiety (e.g., C(=0), C(=S), S(O) or S(0)2) forming the backbone of a ring or ring system.

A compound of Formula 1 in the Summary of the Invention can alternatively be

and l-A-7

The terms "carbocyclic ring", "carbocycle" or "carbocyclic ring system" denote a ring or ring system wherein the atoms forming the ring backbone are selected only from carbon. Unless otherwise indicated, a carbocyclic ring can be a saturated, partially unsaturated, or fully unsaturated ring. When a fully unsaturated carbocyclic ring satisfies Hiickel's rule, then said ring is also called an "aromatic ring". "Saturated carbocyclic" refers to a ring having a backbone consisting of carbon atoms linked to one another by single bonds; unless otherwise specified, the remaining carbon valences are occupied by hydrogen atoms.

The terms "heterocyclic ring", "heterocycle" or "heterocyclic ring system" denote a ring or ring system in which at least one atom forming the ring backbone is not carbon, e.g., nitrogen, oxygen or sulfur. Typically a heterocyclic ring contains no more than 4 nitrogens, no more than 2 oxygens and no more than 2 sulfurs. Unless otherwise indicated, a heterocyclic ring can be a saturated, partially unsaturated, or fully unsaturated ring. When a fully unsaturated heterocyclic ring satisfies Hiickel's rule, then said ring is also called a "heteroaromatic ring" or "aromatic heterocyclic ring". Unless otherwise indicated, heterocyclic rings and ring systems can be attached through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.

"Aromatic" indicates that each of the ring atoms is essentially in the same plane and has a ^-orbital perpendicular to the ring plane, and that (4n + 2) π electrons, where n is a positive integer, are associated with the ring to comply with Hiickel's rule. The term "aromatic ring system" denotes a carbocyclic or heterocyclic ring system in which at least one ring of the ring system is aromatic. The term "aromatic carbocyclic ring system" denotes a carbocyclic ring system in which at least one ring of the ring system is aromatic. The term "aromatic heterocyclic ring system" denotes a heterocyclic ring system in which at least one ring of the ring system is aromatic. The term "nonaromatic ring system" denotes a carbocyclic or heterocyclic ring system that may be fully saturated, as well as partially or fully unsaturated, provided that none of the rings in the ring system are aromatic. The term "nonaromatic carbocyclic ring system" in which no ring in the ring system is aromatic. The term "nonaromatic heterocyclic ring system" denotes a heterocyclic ring system in which no ring in the ring system is aromatic.

The term "optionally substituted" in connection with the heterocyclic rings refers to groups which are unsubstituted or have at least one non-hydrogen substituent that does not extinguish the biological activity possessed by the unsubstituted analog. As used herein, the following definitions shall apply unless otherwise indicated. The term "optionally substituted" is used interchangeably with the phrase "substituted or unsubstituted" or with the term "(un) substituted." Unless otherwise indicated, an optionally substituted group may have a substituent at each substitutable position of the group, and each substitution is independent of the other.

A wide variety of synthetic methods are known in the art to enable preparation of aromatic and nonaromatic heterocyclic rings and ring systems; for extensive reviews see the eight volume set of Comprehensive Heterocyclic Chemistry, A. R. Katritzky and C. W. Rees editors-in-chief, Pergamon Press, Oxford, 1984 and the twelve volume set of Comprehensive Heterocyclic Chemistry II, A. R. Katritzky, C. W. Rees and E. F. V. Scriven editors-in-chief, Pergamon Press, Oxford, 1996.

Compounds of this invention can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers. Stereoisomers are isomers of identical constitution but differing in the arrangement of their atoms in space and include enantiomers, diastereomers, cis-trans isomers (also known as geometric isomers) and atropisomers. Atropisomers result from restricted rotation about single bonds where the rotational barrier is high enough to permit isolation of the isomeric species. One skilled in the art will appreciate that one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers. The compounds of the invention may be present as a mixture of stereoisomers, individual stereoisomers or as an optically active form. For a comprehensive discussion of all aspects of stereoisomerism, see Ernest L. Eliel and Samuel H. Wilen, Stereochemistry of Organic Compounds, John Wiley & Sons, 1994. Compounds of this invention can exist as one or more conformational isomers due to restricted rotation about the amide bond (e.g., C(=A)-R ¹ wherein R ¹ is alkylamino) in Formula 1. This invention comprises mixtures of conformational isomers. In addition, this invention includes compounds that are enriched in one conformer relative to others.

Compounds of Formula 1 typically exist in more than one form, and Formula 1 thus include all crystalline and non-crystalline forms of the compounds they represent. Noncrystalline forms include embodiments which are solids such as waxes and gums as well as embodiments which are liquids such as solutions and melts. Crystalline forms include embodiments which represent essentially a single crystal type and embodiments which represent a mixture of polymorphs (i.e. different crystalline 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 arrangements and/or conformations of the molecules in the crystal lattice. Although polymorphs can have the same chemical composition, they can also differ in composition due the presence or absence of co- crystallized water or other molecules, which can be weakly or strongly bound in the lattice. Polymorphs can differ in such chemical, physical and biological properties as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspensibility, dissolution rate and biological availability. One skilled in the art will appreciate that a polymorph of a compound of Formula 1 can exhibit beneficial effects (e.g., suitability for preparation of useful formulations, improved biological performance) relative to another polymorph or a mixture of polymorphs of the same compound of Formula 1. Preparation and isolation of a particular polymorph of a compound of Formula 1 can be achieved 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, Wiley-VCH, Weinheim, 2006.

One skilled in the art will appreciate that not all nitrogen-containing heterocycles can form N-oxides since the nitrogen requires an available lone pair for oxidation to the oxide; one skilled in the art will recognize those nitrogen-containing heterocycles which can form N-oxides. One skilled in the art will also recognize that tertiary amines can form N-oxides. Synthetic methods for the preparation of N-oxides of heterocycles and tertiary amines are very well known by one skilled in the art including the oxidation of heterocycles and tertiary amines with peroxy acids such as peracetic and w-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethyldioxirane. These methods for the preparation of N-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.

One skilled in the art recognizes that because in the environment and under physiological conditions salts of chemical compounds are in equilibrium with their corresponding nonsalt forms, salts share the biological utility of the nonsalt forms. Thus a wide variety of salts of a compound of Formula 1 are useful for control of undesired vegetation (i.e. are agriculturally suitable). The salts of a compound of Formula 1 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 acids. When a compound of Formula 1 contains an acidic moiety such as a carboxylic acid or phenol, salts also include those formed with organic or inorganic bases such as pyridine, triethylamine or ammonia, or amides, hydrides, hydroxides or carbonates of sodium, potassium, lithium, calcium, magnesium or barium. Accordingly, the present invention comprises compounds selected from Formula 1, N-oxides and agriculturally suitable salts thereof.

Embodiments of the present invention as described in the Summary of the Invention include:

Embodiment 1. A compound of Formula 1 including all all geometric and

stereoisomers, N-oxides, and salts thereof, agricultural compositions containing them and their use as herbicides.

Embodiment 2. A compound of Embodiment 1 wherein A is A-l, A-2, A-3 or A-5. Embodiment 3. A compound of Embodiment 2 wherein A is A-l, A-2 or A-5.

Embodiment 4. A compound of Embodiment 3 wherein A is A-l or A-2.

Embodiment 5. A compound of Embodiment 1 wherein A is A-l or A-3.

Embodiment 6. A compound of Embodiment 1 wherein A is A-l .

Embodiment 7. A compound of Embodiment 1 wherein A is A-2.

Embodiment 8. A compound of Embodiment 1 wherein A is A-3.

Embodiment 9. A compound of Embodiment 1 wherein A is A-4.

Embodiment 10. A compound of Embodiment 1 wherein A is A-5.

Embodiment 11. A compound of Embodiment 1 wherein A is A-6.

Embodiment 12. A compound of Embodiment 1 wherein A is A-7.

Embodiment 13. A compound of any one of Embodiments 1, 2, 5 or 8 wherein B is O.

Embodiment 14. A compound of Formula 1 or any one of Embodiments 1 through 14 either alone or in combination, wherein R ¹ is Ci-Cg alkyl, C2-Cg alkenyl, C2-Cg alkynyl, Ci-Cg haloalkyl, C2-Cg haloalkenyl, C2-Cg haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C3-C6 halocycloalkylalkyl, C4-C8 alkylcycloalkyl, C4-C8 cycloalkylalkyl, Ci-Cg alkylamino, Ci-Cg

haloalkylamino, C2-C ₁ 0 dialkylamino, C2-C ₁ 0 halodialkylamino, Ci-Cg alkoxy, C3-C6 alkenyloxy, C3-C6 alkynyloxy, Ci-Cg haloalkoxy, C3-C6

haloalkenyloxy, C3-C6 haloalkynyloxy, C3-C6 cycloalkoxy, C3-C6

halocycloalkoxy, C4-C8 cycloalkylalkoxy, C4-C8 halocycloalkylalkoxy, C2-Cg alkoxyalkyl, C2-Cg haloalkoxyalkyl, C2-Cg alkoxyhaloalkyl, C2-Cg

alkoxyalkoxy, C2-Cg cyanoalkyl, C2-Cg cyanoalkoxy, C3-C7 cyanoalkoxyalkyl, Ci-Cg hydroxyalkyl, Ci-Cg nitroalkyl, Ci-Cg alkylthio, Ci-Cg haloalkylthio, C3-C8 cycloalkylthio, Ci-Cg alkenylthio, Ci-Cg alkylsulfinyl, Ci-Cg haloalkylsulfinyl, Ci-Cg alkylsulfonyl, Ci-Cg haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C2-Cg alkylthioalkyl, C2-Cg haloalkylthioalkyl, benzyl, -N(R ⁷ )(OR ⁸ ), -ON(R ^9a )(R ^9b ) or -N(R ⁷ )N(R ^9a )(R ^9b ).

Embodiment 15. A compound of Embodiment 14 wherein R ¹ is Ci-Cg alkyl, C2-Cg alkenyl, C2-Cg alkynyl, Ci-Cg haloalkyl, C2-Cg haloalkenyl, C2-Cg

haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C3-C6

halocycloalkylalkyl, C4-C8 alkylcycloalkyl, C4-C8 cycloalkylalkyl, Ci-Cg alkylamino, Ci-Cg haloalkylamino, C2-C ₁ 0 dialkylamino, C2-C ₁ 0

halodialkylamino, Ci-Cg alkoxy, C3-C6 alkenyloxy, C3-C6 alkynyloxy, Ci-Cg haloalkoxy, C3-C6 haloalkenyloxy, C3-C6 haloalkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C4-C8 cycloalkylalkoxy, C4-C8 halocycloalkylalkoxy, C2-Cg alkoxyalkyl, C2-Cg haloalkoxyalkyl, C2-Cg alkoxyhaloalkyl, C2-Cg alkoxyalkoxy, C2-Cg cyanoalkyl, C2-Cg cyanoalkoxy, C3-C7 cyanoalkoxyalkyl, Ci-Cg hydroxyalkyl, Ci-Cg nitroalkyl, Ci-Cg alkylthio, Ci-Cg haloalkylthio, C3-C8 cycloalkylthio, Ci-Cg alkenylthio, Ci-Cg alkylsulfinyl, Ci-Cg haloalkylsulfinyl, Ci-Cg alkylsulfonyl, Ci-Cg haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C2-Cg alkylthioalkyl or C2-Cg haloalkylthioalkyl.

Embodiment 16. A compound of Embodiment 15 wherein R ¹ is Ci-Cg alkyl, C2-Cg alkenyl, C2-Cg alkynyl, Ci-Cg haloalkyl, Ci-Cg alkoxy, C3-C6 alkenyloxy, C3-C6 alkynyloxy, Ci-Cg haloalkoxy, C3-C6 haloalkenyloxy, C3-C6 cycloalkoxy, C4-C8 cycloalkylalkoxy, C2-Cg cyanoalkyl, C2-Cg cyanoalkoxy, Ci-Cg alkylthio, Ci-Cg haloalkylthio or Ci-Cg alkenylthio.

Embodiment 17. A compound of Embodiment 16 wherein R ¹ is Ci-Cg alkyl, C2-Cg alkenyl, C2-Cg alkynyl, Ci-Cg haloalkyl, Ci-Cg alkoxy, C3-C6 alkenyloxy, C3-C6 alkynyloxy, Ci-Cg haloalkoxy, C3-C6 haloalkenyloxy, C2-Cg cyanoalkyl, C2-Cg cyanoalkoxy, Ci-Cg alkylthio, Ci-Cg haloalkylthio or Ci-Cg alkenylthio. Embodiment 18. A compound of Embodiment 17 wherein R ¹ is Ci-Cg alkyl, C2-Cg alkenyl, C2-Cg alkynyl, Ci-Cg haloalkyl, Ci-Cg alkoxy, C3-C6 alkenyloxy,

C3-C6 alkynyloxy, Ci-Cg haloalkoxy, C3-C6 haloalkenyloxy, Ci-Cg alkylthio,

Ci-Cg haloalkylthio or Ci-Cg alkenylthio.

Embodiment 19. A compound of Embodiment 17 wherein R ¹ is Ci-Cg alkyl, C2-Cg alkenyl, C2-Cg alkynyl, Ci-Cg haloalkyl, Ci-Cg alkoxy, C3-C6 alkenyloxy,

C3-C6 alkynyloxy or C3-C6 haloalkenyloxy.

Embodiment 20. A compound of Embodiment 19 wherein R ¹ is Ci-Cg alkyl, C2-Cg alkenyl, Ci-Cg haloalkyl, Ci-Cg alkoxy or Ci-Cg haloalkoxy.

Embodiment 21. A compound of Embodiment 20 wherein R ¹ is Ci-Cg alkyl, Ci-Cg haloalkyl, Ci-Cg alkoxy or Ci-Cg haloalkoxy.

Embodiment 22. A compound of Embodiment 21 wherein R ¹ is Ci-Cg alkyl.

Embodiment 23. A compound of Embodiment 21 wherein R ¹ is Ci-Cg haloalkyl. Embodiment 24. A compound of Embodiment 21 wherein R ¹ is Ci-Cg alkoxy.

Embodiment 25. A compound of Embodiment 21 wherein R ¹ is C2-Cg haloalkoxy.

Embodiment 26. A compound of Embodiment 21 wherein R ¹ is C4-C6 alkyl, C3-C6 haloalkyl, C3-C6 alkoxy or C3-C6 haloalkoxy.

Embodiment 27. A compound of Embodiment 26 wherein when A is A-3 then R ¹ is

C3-C6 haloalkyl.

Embodiment 28. A compound of Embodiment 26 wherein when A is A-l then R ¹ is

C4-C6 haloalkyl.

Embodiment 29. A compound of Embodiment 28 wherein when A is A-l then R ¹ is C4-C5 haloalkyl.

Embodiment 30. A compound of Embodiment 29 wherein when A is A-l then R ¹ is CH2CH2CH2CF3.

Embodiment 31. A compound of Embodiment 29 wherein when A is A-l then R ¹ is CH2CH2CF2CF3.

Embodiment 32. A compound of Embodiment 19 wherein when A is A-3 then R ¹ is C4-C6 haloalkenyloxy.

Embodiment 33. A compound of Embodiment 26 wherein when A is A-3 then R ¹ is

C4-C5 haloalkoxy.

Embodiment 34. A compound of Embodiment 23 wherein R ¹ is

CH2CH2CH2CH2CH2CF3.

Embodiment 35. A compound of Embodiment 23 wherein R ¹ is

CH2CH2CH2CH2CF3.

Embodiment 36. A compound of Embodiment 23 wherein R ¹ is CH2CH2CH2CF3. Embodiment 37. A compound of Embodiment 23 wherein R ¹ is CH2CH2CF3. Embodiment 38. A compound of Embodiment 25 wherein R ¹ is

OCH ₂ CH ₂ CH ₂ CH ₂ CF ₃ .

Embodiment 39. A compound of Embodiment 25 wherein R ¹ is OCH ₂ CH ₂ CH ₂ CF3. Embodiment 40. A compound of Embodiment 25 wherein R ¹ is OCH ₂ CH ₂ CF3.

Embodiment 41. A compound of Embodiment 25 wherein RMs OCH ₂ CF ₂ CF ₃ .

Embodiment 42. A compound of any one Embodiments 1 through 13 wherein R ¹ is other than H.

Embodiment 43. A compound of any one Embodiments 1 through 14 wherein R ¹ is other than benzyl (unsubstituted).

Embodiment 44. A compound of any one Embodiments 1 through 22 wherein R ¹ is other than CH ₃ , CH ₂ CH ₃ or CH ₂ CH ₂ CH ₃ .

Embodiment 45. A compound of any one Embodiments 1 through 20 or wherein R ¹ is other than CH ₂ CH=CH ₂ , CH=CHCH ₃ , C(=CH ₂ )CH ₃ or CH=C(CH ₃ ) ₂

Embodiment 46. A compound of Embodiment 1 wherein R ¹ is other than propen-2-yl, propen-l-yl, ^-propyl, ethyl, l-methylethen-2-yl or 2-methylpropen-l-yl (i.e. R ¹ is other than CH ₂ CH=CH ₂ , CH ₂ CH ₂ CH ₃ , CH=CHCH ₃ , CH ₂ CH ₃ ,

C(=CH ₂ )CH ₃ or CH=C(CH ₃ ) ₂ .

Embodiment 47. A compound of any one Embodiments 1 through 22 or 24 wherein

R ¹ is other than OCH ₃ .

Embodiment 48. A compound of Formula 1 or any one of Embodiments 1 through 47 either alone or in combination, wherein Z is O.

Embodiment 49. A compound of Formula 1 or any one of Embodiments 1 through 48 either alone or in combination, wherein R ² is halogen, C1-C4 alkyl or C 1-C4 haloalkyl.

Embodiment 50. A compound of Embodiment 49 wherein R ² is halogen or C1-C4 alkyl.

Embodiment 51. A compound of Embodiment 50 wherein R ² is halogen or CH ₃ .

Embodiment 52. A compound of Embodiment 51 wherein R ² is halogen.

Embodiment 53. A compound of Embodiment 52 wherein R ² is F, CI or Br.

Embodiment 54. A compound of Embodiment 53 wherein R ² is CI.

Embodiment 55. A compound of Formula 1 or any one of Embodiments 1 through 54 either alone or in combination, wherein m is 0, 1 or 2.

Embodiment 56. A compound of Embodiment 55 wherein m is 0 or 1.

Embodiment 57. A compound of Embodiment 56 wherein m is 1.

Embodiment 58. A compound of Embodiment 57 wherein m is 1, at the 3, 4 or 6- position.

Embodiment 59. A compound of Embodiment 58 wherein m is 1, at the 3 or 4- position. Embodiment 60. A compound of Embodiment 59 wherein m is 0 (i.e. each of the 3-, 4-, 5- and 6-positions are unsubtituted by R ³ ).

Embodiment 61. A compound of Formula 1 or any one of Embodiments 1 through 60 either alone or in combination, wherein each R ³ is independently halogen, cyano, CHO, C1-C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ alkynyl, C1-C ₄ haloalkyl, C ₂ -C ₄ haloalkenyl, C2-C4 haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C4-C8 alkylcycloalkyl, C ₂ -Cg alkylcarbonyl, C ₂ -Cg haloalkylcarbonyl, C ₂ -Cg alkoxycarbonyl, C1-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C4 haloalkoxy, C3-C4 haloalkenyloxy, C3-C4 haloalkynyloxy, C3-C6 cycloalkoxy, 3-C6 halocycloalkoxy, C ₂ -Cg alkoxyalkyl, C ₂ -Cg haloalkoxyalkyl, C ₂ -C4 alkylcarbonyloxy, C ₂ -C ₆ cyanoalkyl, -C(=0)N(R ^{l la} R ^{l lb} ), -C(=NOR ¹² )H or -SO _n R ¹⁴ .

Embodiment 62. A compound of Embodiment 61 wherein each R ³ is independently halogen, cyano, CHO, C 1-C4 alkyl, C ₂ -C4 alkenyl, C ₂ -C4 alkynyl, C 1-C4 haloalkyl, C ₂ -C4 haloalkenyl, C ₂ -C4 haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C ₂ -Cg alkylcarbonyl, C ₂ -Cg haloalkylcarbonyl, C ₂ -Cg alkoxycarbonyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C ₂ -Cg alkoxyalkyl, C ₂ -Cg haloalkoxyalkyl, C ₂ -Cg cyanoalkyl or -SO _n R ¹⁴ .

Embodiment 63. A compound of Embodiment 62 wherein each R ³ is independently halogen, cyano, C1-C4 alkyl or C 1-C4 haloalkyl.

Embodiment 64. A compound of Embodiment 63 wherein each R ³ is independently halogen, cyano, C1-C3 alkyl or C 1-C3 haloalkyl.

Embodiment 65. A compound of Embodiment 64 wherein each R ³ is independently halogen, cyano, Ci-C ₂ alkyl or Ci-C ₂ haloalkyl.

Embodiment 66. A compound of Embodiment 65 wherein each R ³ is independently halogen, cyano, CH ₃ , CH ₂ CH ₃ or CF ₃ .

Embodiment 67. A compound of Embodiment 66 wherein each R ³ is independently halogen, cyano or CF ₃ .

Embodiment 68. A compound of Embodiment 67 wherein each R ³ is independently F, CI, Br or cyano.

Embodiment 69. A compound of Embodiment 68 wherein each R ³ is independently

Br or cyano.

Embodiment 70. A compound of Embodiment 69 wherein each R ³ is independently halogen or cyano.

Embodiment 71. A compound of Embodiment 70 wherein each R ³ is independently cyano.

Embodiment 72. A compound of Embodiment 70 wherein each R ³ is independently halogen. Embodiment 73. A compound of Embodiment 72 wherein each R ³ is independently

Br.

Embodiment 74. A compound of Formula 1 or any one of Embodiments 1 through 73 either alone or in combination, wherein m is at least 1 and one R ³ is located at the 3-position (i.e. adjacent to the -AR ¹ group) represented by the compound of Formula ID

wherein A, R ¹ , R ² and Z are as defined in the Summary of the Invention or in any one of Embodiments 1 through 59;

R ^3a is as defined for R ³ in any one of Embodiments 61 through 73;

R ^b is as defined for R ³ in any one of Embodiments 61 through 73; and

p is is 0 or 1.

Embodiment 75. A compound of Embodiment 74 wherein p is 1; R ^3a is halogen, cyano, C 1-C3 alkyl, C 1-C3 haloalkyl or C1-C3 alkoxy; and R ^b is halogen, cyano, C 1-C3 alkyl, C 1-C3 haloalkyl or C1-C3 alkoxy.

Embodiment 76. A compound of Embodiment 75 wherein p is 0 and R ^3a is halogen, cyano, C 1-C3 alkyl, C 1-C3 haloalkyl or C1-C3 alkoxy.

Embodiment 77. A compound of Embodiment 76 wherein R ^3a is halogen or cyano.

Embodiment 78. A compound of Embodiment 77 wherein R ^3a is Br or cyano.

Embodiment 79. A compound of Formula 1 or any one of Embodiments 1 through 28 either alone or in combination, wherein R ⁵ is H, C i -Cg alkyl, C2-Cg alkenyl, C2-Cg alkynyl, Ci -Cg haloalkyl, C2-Cg haloalkenyl, C2-Cg haloalkynyl, C2-Cg alkoxyalkyl, C2-Cg haloalkoxyalkyl, C2-Cg cyanoalkyl, C3-C7

cyanoalkoxyalkyl, C2-Cg alkylthioalkyl or C2-Cg haloalkylthioalkyl.

Embodiment 80. A compound of Embodiment 79 wherein R ⁵ is C i -Cg alkyl or

Ci -Cg haloalkyl.

Embodiment 81. A compound of Embodiment 1 wherein when A is A-5, then R ³ is in the 4-, 5- or 6- position.

Embodiment 82. A compound of Embodiment 1 wherein when A is A-3, B is O, R ³ is

3-Br then R ¹ is other then 3-bromopropane. Embodiment 83. A compound of Embodiment 1 wherein when A is A-3, R ³ is halogen at the 3 -position.

Embodiment 84. A compound of Embodiment 1 wherein when A is A-l, R ³ is cyano at the 3 -position.

Embodiment 85. A compound of Embodiment 1 wherein R ¹ is other than C ₃ -C6

cycloamino.

Embodiment 86. A compound of Embodiment 1 wherein each R ^{l la} is independently

Ci-C ₂ ^alk y! ^c l ^"c 2 haloalkyl.

Embodiment 87. A compound of Embodiment 1 wherein each R ^{1 1 5} is independently

Ci-C ₂ ^alk y! ^{or c} l ^"c 2 haloalkyl.

Embodiment 88. A compound of Embodimentl wherein each R ¹² is independently H or C!-C ₃ alkyl.

Embodiment 89. A compound of Embodiment 1 wherein each R ¹⁴ is independently

C1-C3 alkyl or C1-C3 haloalkyl.

Embodiment 90. A compound of Embodiment 1 wherein each R ¹⁴ is independently

C1-C3 alkyl.

Embodiment 91. A compound of Embodiment 1 wherein m is 1, 2 or 3.

Embodiment 92. A compound of Embodiment 1 wherein m is 1 or 2.

Embodiments of this invention, including Embodiments 1-92 above as well as any other embodiments described herein, can be combined in any manner, and the descriptions of variables in the embodiments pertain not only to the compounds of Formula 1 but also to the starting compounds and intermediate compounds useful for preparing the compounds of Formula 1. In addition, embodiments of this invention, including Embodiments 1-92 above as well as any other embodiments described herein, and any combination thereof, pertain to the compositions and methods of the present invention.

Combinations of Embodiments 1-92 are illustrated by:

Embodiment A. A compound of Formula 1 wherein

A is A-l, A-2, A-3 or A-5;

R ¹ is R ¹ is C!-C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C _x -C ₆ haloalkyl, C ₂ -C ₆

haloalkenyl, C ₂ -Cg haloalkynyl, C ₃ -Cg cycloalkyl, C ₃ -Cg halocycloalkyl, C ₃ - Cg halocycloalkylalkyl, C^-Cg alkylcycloalkyl, C^-Cg cycloalkylalkyl, Ci-Cg alkylamino, Ci-Cg haloalkylamino, C ₂ -C I Q dialkylamino, C ₂ -CI Q

halodialkylamino, Ci-Cg alkoxy, C ₃ -Cg alkenyloxy, C ₃ -Cg alkynyloxy, Ci-Cg haloalkoxy, C ₃ -Cg haloalkenyloxy, C ₃ -Cg haloalkynyloxy, C ₃ -Cg cycloalkoxy, C ₃ -Cg halocycloalkoxy, C^-Cg cycloalkylalkoxy, C^-Cg halocycloalkylalkoxy, C ₂ -Cg alkoxyalkyl, C ₂ -Cg haloalkoxyalkyl, C ₂ -Cg alkoxyhaloalkyl, C ₂ -Cg alkoxyalkoxy, C ₂ -Cg cyanoalkyl, C ₂ -Cg cyanoalkoxy, C ₃ -C ₇ cyanoalkoxyalkyl, Ci-Cg hydroxyalkyl, Ci-Cg nitroalkyl, Ci-Cg alkylthio, Ci-Cg haloalkylthio, C3-C8 cycloalkylthio, Ci-Cg alkenylthio, Ci-Cg alkylsulfinyl, C i-Cg haloalkylsulfinyl, Ci-Cg alkylsulfonyl, Ci-Cg haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C2-Cg alkylthioalkyl or C2-Cg haloalkylthioalkyl; R ² is halogen, C1-C4 alkyl or C 1-C4 haloalkyl;

each R ³ is independently halogen, cyano, CHO, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C 1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C4-C8 alkylcycloalkyl, C2-Cg alkylcarbonyl, C2-Cg haloalkylcarbonyl, C2-Cg alkoxycarbonyl, C1-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C 1-C4 haloalkoxy, C3-C4 haloalkenyloxy, C3-C4 haloalkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C2-Cg alkoxyalkyl, C2-Cg haloalkoxyalkyl, C2-C4 alkylcarbonyloxy, C2-Cg cyanoalkyl, -C(=0)N(R ^{l la} R ^{l lb} ), -C(=NOR ¹² )H or -SO _n R ¹⁴ ;

R ⁵ is H, C _x -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C _x -C ₆ haloalkyl, C ₂ -C ₆

haloalkenyl, C2-Cg haloalkynyl, C2-Cg alkoxyalkyl, C2-Cg haloalkoxyalkyl, C2-Cg cyanoalkyl, C3-C7 cyanoalkoxyalkyl, C2-Cg alkylthioalkyl or C2-Cg haloalkylthioalkyl;

R ^{l la} is C!-C ₂ alkyl C!-C ₂ haloalkyl;

R ^{l lb} is C!-C ₂ alkyl or C!-C ₂ haloalkyl;

R ¹² is H or Ci-C ₃ alkyl; and

R ¹⁴ is C!-C ₃ alkyl or C!-C ₃ haloalkyl.

Embodiment B . A compound of Embodiment A wherein

A is A-l, A-2 or A-5;

R ¹ is Ci-Cg alkyl, C2-Cg alkenyl, C2-Cg alkynyl, C i-Cg haloalkyl, C i-Cg alkoxy, C3-C6 alkenyloxy, C3-C6 alkynyloxy, Ci-Cg haloalkoxy, C3-C6

haloalkenyloxy, C3-C6 cycloalkoxy, C4-C8 cycloalkylalkoxy, C2-Cg cyanoalkyl, C2-Cg cyanoalkoxy, Ci-Cg alkylthio, C i-Cg haloalkylthio or Ci-Cg alkenylthio;

R ² is halogen or C1-C4 alkyl;

each R ³ is independently halogen, cyano, CHO, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C 1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-Cg alkylcarbonyl, C2-Cg

haloalkylcarbonyl, C2-Cg alkoxycarbonyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-Cg alkoxyalkyl, C2-Cg haloalkoxyalkyl, C2-Cg cyanoalkyl or -SO _n R ¹⁴ ;

R ⁵ is C!-C ₆ alkyl or C!-C ₆ haloalkyl;

each R ¹⁴ is independently C1-C3 alkyl; and

m is 0, 1 or 2.

Embodiment C. A compound of Embodiment B wherein

A is A-l or A-2; R ¹ is Ci-Cg alkyl, C2-Cg alkenyl, C2-Cg alkynyl, Ci-Cg haloalkyl, Ci-Cg alkoxy, C3-C6 alkenyloxy, C3-C6 alkynyloxy, Ci-Cg haloalkoxy, C3-C6

haloalkenyloxy, C2-Cg cyanoalkyl, C2-Cg cyanoalkoxy, Ci-Cg alkylthio, C\- Cg haloalkylthio or Ci-Cg alkenylthio;

R ² is halogen or CH ₃ ; and

each R ³ is independently halogen, cyano, C1-C4 alkyl or C 1-C4 haloalkyl.

Embodiment D. A compound of Embodiment C wherein

A is A-l ;

R ¹ is Ci-Cg alkyl, C2-Cg alkenyl, C2-Cg alkynyl, Ci-Cg haloalkyl, Ci-Cg alkoxy, 3-C6 alkenyloxy, C3-C6 alkynyloxy, Ci-Cg haloalkoxy, C3-C6 haloalkenyloxy, Ci-Cg alkylthio, Ci-Cg haloalkylthio or Ci-Cg alkenylthio; Z is O;

R ² is halogen;

each R ³ is independently halogen, cyano, C1-C3 alkyl or C 1-C3 haloalkyl; and m is 1 or 2.

Embodiment E. A compound of Embodiment C wherein

A is A-2;

R ¹ is Ci-Cg alkyl, C2-Cg alkenyl, Ci-Cg haloalkyl, Ci-Cg alkoxy or Ci-Cg

haloalkoxy;

Z is O;

R ² is F, CI or Br;

each R ³ is independently halogen, cyano, C1-C2 alkyl or C 1-C2 haloalkyl; and m is 0 or 1.

Embodiment F. A compound of Embodiment A wherein

A is A-3;

R ¹ is Ci-Cg alkyl, C2-Cg alkenyl, C2-Cg alkynyl, Ci-Cg haloalkyl, Ci-Cg alkoxy, C3-C6 alkenyloxy, C3-C6 alkynyloxy, Ci-Cg haloalkoxy, C3-C6

haloalkenyloxy, C3-C6 cycloalkoxy, C4-C8 cycloalkylalkoxy, C2-Cg cyanoalkyl, C2-Cg cyanoalkoxy, Ci-Cg alkylthio, Ci-Cg haloalkylthio or Ci-Cg alkenylthio;

R ² is halogen or C1-C4 alkyl;

each R ³ is independently halogen, cyano, C1-C4 alkyl or C 1-C4 haloalkyl; and m is 1 or 2.

Embodiment G. A compound of Embodiment F wherein

B is O;

R ¹ is Ci-Cg alkyl, C2-Cg alkenyl, C2-Cg alkynyl, Ci-Cg haloalkyl, Ci-Cg alkoxy, C3-C6 alkenyloxy, C3-C6 alkynyloxy, Ci-Cg haloalkoxy, C3-C6 haloalkenyloxy, C2-Cg cyanoalkyl, C2-Cg cyanoalkoxy, Ci-Cg alkylthio, C - Cg haloalkylthio or Ci-Cg alkenylthio;

Z is O;

R ² is halogen or CH ₃ ;

each R ³ is independently halogen, cyano, C1 -C3 alkyl or C 1 -C3 haloalkyl; and m is 1 or 2.

Specific embodiments include compounds of Formula 1 selected from the group consisting of:

3,3,3-trifluoropropyl 2-chloro-6-[(5-chloro-2-pyrimidinyl)oxy]benzoate (Compound 15);

3.3.3- trifluoro-l-methylpropyl 2-bromo-6-[(5-chloro-2-pyrimidinyl)oxy]benzoate

(Compound 16);

propyl 2-bromo-6-[(5-chloro-2-pyrimidinyl)oxy]benzoate (Compound 13);

4.4.4- trifluorobutyl 2-bromo-6-[(5-chloro-2-pyrimidinyl)oxy]benzoate (Compound 20);

2- propen-l-yl 2-bromo-6-[(5-chloro-2-pyrimidinyl)oxy]benzoate (Compound 22);

3- buten-l-yl 2-bromo-6-[(5-chloro-2-pyrimidinyl)oxy]benzoate (Compound 21);

2,2,3,3,3-pentafluoropropyl 2-bromo-6-[(5-chloro-2-pyrimidinyl)oxy]benzoate (Compound 23);

3,3,3-trifluoropropyl 2-bromo-6-[(5-chloro-2-pyrimidinyl)oxy]benzoate (Compound 26); l-[2-chloro-6-[(5-chloro-2-pyrimidinyl)oxy]phenyl]-4,4,4-tri fluoro-l-butanone (Compound 107); and

3-[(5-chloro-2-pyrimidinyl)oxy]-2-(5,5,5-trifluoropentyl)ben zonitrile (Compound 73).

Embodiments of the present invention as described in the Summary of the Invention include (where Formula IP as used in the following Embodiments includes N-oxides and salts thereof):

Embodiment PI . A compound of Formula IP wherein A is H ₂ , O, S or N(OR ⁵ ). Embodiment P2. A compound of Embodiment PI wherein A is H ₂ , O or N(OR ⁵ ). Embodiment P3. A compound of Embodiment P2 wherein A is O or N(OR ⁵ ).

Embodiment P4. A compound of Embodiment P3 wherein A is O.

Embodiment P5. A compound of Embodiment P3 wherein A is N(OR ⁵ ). Embodiment P6. A compound of Formula IP or any one of Embodiments PI through P5 either alone or in combination, wherein R ¹ is Ci-Cg alkyl, C2-Cg alkenyl, C2-Cg alkynyl, Ci-Cg haloalkyl, C2-Cg haloalkenyl, C2-Cg haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C4-C8 alkylcycloalkyl, C4-C8

cycloalkylalkyl, Ci-Cg alkylamino, Ci-Cg haloalkylamino, C2-C ₁ 0

dialkylamino, C2-C ₁ 0 halodialkylamino, C3-C6 cycloamino, Ci-Cg alkoxy, C3-C6 alkenyloxy, C3-C6 alkynyloxy, Ci-Cg haloalkoxy, C3-C6

haloalkenyloxy, C3-C6 haloalkynyloxy, C3-C6 cycloalkoxy, C3-C6

halocycloalkoxy, C4-C8 cycloalkylalkoxy, C4-C8 halocycloalkylalkoxy, C2-Cg alkoxyalkyl, C2-Cg haloalkoxyalkyl, C2-Cg alkoxyhaloalkyl, C2-Cg

alkoxyalkoxy, C2-Cg cyanoalkyl, C2-Cg cyanoalkoxy, C3-C7 cyanoalkoxyalkyl, Ci-Cg hydroxyalkyl, Ci-Cg nitroalkyl, Ci-Cg alkylthio, Ci-Cg haloalkylthio, C3-C8 cycloalkylthio, Ci-Cg alkylsulfinyl, Ci-Cg haloalkylsulfinyl, Ci-Cg alkylsulfonyl, Ci-Cg haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C2-Cg alkylthioalkyl, C ₂ -C ₆ haloalkylthioalkyl, benzyl, - R ⁷ OR ⁸ , -ON(R ^9a R ^9b ) or - R ⁷ N(R ^9a R ^9b ).

Embodiment P7. A compound of Embodiment P6 wherein R ¹ is Ci-Cg alkyl, C2-Cg alkenyl, C2-Cg alkynyl, Ci-Cg haloalkyl, C2-Cg haloalkenyl, C2-Cg

haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C4-C8 alkylcycloalkyl, C4-C8 cycloalkylalkyl, Ci-Cg alkylamino, Ci-Cg haloalkylamino, C2-C ₁ 0 dialkylamino, C2-C ₁ 0 halodialkylamino, C3-C6 cycloamino, Ci-Cg alkoxy, C3-C6 alkenyloxy, C3-C6 alkynyloxy, Ci-Cg haloalkoxy, C3-C6

haloalkenyloxy, C3-C6 haloalkynyloxy, C3-C6 cycloalkoxy, C3-C6

halocycloalkoxy, C4-C8 cycloalkylalkoxy, C4-C8 halocycloalkylalkoxy, C2-Cg alkoxyalkyl, C2-Cg haloalkoxyalkyl, C2-Cg alkoxyhaloalkyl, C2-Cg

alkoxyalkoxy, C2-Cg cyanoalkyl, C2-Cg cyanoalkoxy, C3-C7 cyanoalkoxyalkyl, Ci-Cg hydroxyalkyl, Ci-Cg nitroalkyl, Ci-Cg alkylthio, Ci-Cg haloalkylthio, C3-C8 cycloalkylthio, Ci-Cg alkylsulfinyl, Ci-Cg haloalkylsulfinyl, Ci-Cg alkylsulfonyl, Ci-Cg haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C2-Cg alkylthioalkyl or C2-Cg haloalkylthioalkyl.

Embodiment P8. A compound of Embodiment P7 wherein R ¹ is Ci-Cg alkyl, C2-Cg alkenyl, C2-Cg alkynyl, Ci-Cg haloalkyl, C2-Cg haloalkenyl, C2-Cg

haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, Ci-Cg alkoxy, C3-C6 alkenyloxy, C3-C6 alkynyloxy, Ci-Cg haloalkoxy, C3-C6 haloalkenyloxy, C3-C6 haloalkynyloxy or C3-C6 cycloalkoxy.

Embodiment P9. A compound of Embodiment P8 wherein R ¹ is Ci-Cg alkoxy,

C3-C6 alkenyloxy, C3-C6 alkynyloxy, Ci-Cg haloalkoxy, C3-C6

haloalkenyloxy, C3-C6 haloalkynyloxy or C3-C6 cycloalkoxy. Embodiment P10. A compound of Formula IP or any one of Embodiments PI through P9 either alone or in combination, wherein Z is O.

Embodiment PI 1. A compound of Formula IP or any one of Embodiments PI

through P10 either alone or in combination, wherein R ² is halogen, C 1-C4 alkyl or C 1-C4 haloalkyl.

Embodiment P12. A compound of Embodiment PI 1 wherein R ² is halogen or C1-C4 alkyl.

Embodiment P13. A compound of Embodiment P 12 wherein R ² is halogen or CH3. Embodiment P14. A compound of Embodiment P13 wherein R ² is halogen.

Embodiment PI 5. A compound of Embodiment P14 wherein R ² is F, CI or Br.

Embodiment PI 6. A compound of Formula IP or any one of Embodiments PI

through PI 5 either alone or in combination, wherein m is 0, 1 or 2.

Embodiment P17. A compound of Embodiment P16 wherein m is 0 or 1.

Embodiment PI 8. A compound of Embodiment P17 wherein m is 1.

Embodiment P19. A compound of Embodiment P17 wherein m is 0 (i.e. the 3-, 4-, 5- and 6-positions are unsubtituted by R ³ ).

Embodiment P20. A compound of Formula IP or any one of Embodiments PI

through P19 either alone or in combination, wherein each R ³ is independently halogen, cyano, CHO, C 1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C 1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C4-C8 alkylcycloalkyl, C2-Cg alkylcarbonyl, C2-Cg

haloalkylcarbonyl, C2-Cg alkoxycarbonyl, C1-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C4 haloalkoxy, C3-C4 haloalkenyloxy, C3-C4 haloalkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C2-Cg alkoxyalkyl, C2-Cg haloalkoxyalkyl, C2-C4 alkylcarbonyloxy, C2-Cg cyanoalkyl, -C(=0)N(R ^{l la} R ^{l lb} ), -C(=NOR ¹² )H or -SO _n R ¹⁴ .

Embodiment P21. A compound of Embodiment P20 wherein each R ³ is independently halogen, cyano, CHO, C 1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C 1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-Cg alkylcarbonyl, C2-Cg haloalkylcarbonyl, C2-Cg alkoxycarbonyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-Cg alkoxyalkyl, C2-Cg haloalkoxyalkyl, C2-Cg cyanoalkyl or -SO _n R ¹⁴ .

Embodiment P22. A compound of Embodiment P21 wherein each R ³ is independently halogen, cyano, C1-C4 alkyl or C 1-C4 haloalkyl.

Embodiment P23. A compound of Embodiment P22 wherein each R ³ is independently halogen or cyano.

Embodiment P24. A compound of Embodiment P23 wherein each R ³ is independently cyano. Embodiment P25. A compound of Embodiment P23 wherein each R ³ is independently halogen.

Embodiment P26. A compound of Embodiment P23 wherein each R ³ is independently Br.

Embodiment P27. A compound of Formula IP or any one of Embodiments PI

through P26 either alone or in combination, wherein m is 1 and R ³ is located at the 3-position (i.e. adjacent to the C(=A)R ¹ group).

Embodiment P28. A compound of Formula IP or any one of Embodiments PI

through P26 either alone or in combination, wherein m is 2 and R ³ is located at the 3- and the 6-position (i.e. adjacent to the C(=A)R ¹ group and the

Z(pyrimidine group).

Embodiment P29. A compound of Formula IP or any one of Embodiments PI

through P28 either alone or in combination, wherein R ⁵ is H, Ci-Cg alkyl,

C2-Cg alkenyl, C2-Cg alkynyl, Ci-Cg haloalkyl, C2-Cg haloalkenyl, C2-Cg haloalkynyl, C2-Cg alkoxyalkyl, C2-Cg haloalkoxyalkyl, C2-Cg cyanoalkyl,

C3-C7 cyanoalkoxyalkyl, C2-Cg alkylthioalkyl or C2-Cg haloalkylthioalkyl. Embodiment P30. A compound of Embodiment P29 wherein R ⁵ is Ci-Cg alkyl, or Ci-Cg haloalkyl.

Embodiments of this invention, including Embodiments P1-P30 above as well as any other embodiments described herein, can be combined in any manner, and the descriptions of variables in the embodiments pertain not only to the compounds of Formula IP but also to the starting compounds and intermediate compounds useful for preparing the compounds of Formula IP. In addition, embodiments of this invention, including Embodiments P1-P30 above as well as any other embodiments described herein, and any combination thereof, pertain to the compositions and methods of the present invention.

Combinations of Embodiments P1-P30 are illustrated by:

Embodiment PA. A compound of Formula IP wherein

A is H ₂ , O, S or N(OR ⁵ );

R ¹ is C _x -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, Ci-C ₆ haloalkyl, C ₂ -C ₆

haloalkenyl, C2-Cg haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl,

C4-C8 alkylcycloalkyl, C^-Cg cycloalkylalkyl, Ci-Cg alkylamino, Ci-Cg haloalkylamino, C2-C ₁ 0 dialkylamino, C2-C ₁ 0 halodialkylamino, C3-C6 cycloamino, Ci-Cg alkoxy, C3-C6 alkenyloxy, C3-C6 alkynyloxy, Ci-Cg haloalkoxy, C3-C6 haloalkenyloxy, C3-C6 haloalkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C^-Cg cycloalkylalkoxy, Cz _j -Cg halocycloalkylalkoxy,

C2-Cg alkoxyalkyl, C2-Cg haloalkoxyalkyl, C2-Cg alkoxyhaloalkyl, C2-Cg alkoxyalkoxy, C2-Cg cyanoalkyl, C2-Cg cyanoalkoxy, C3-C7 cyanoalkoxyalkyl, Ci-Cg hydroxyalkyl, Ci-Cg nitroalkyl, Ci-Cg alkylthio, Ci-Cg haloalkylthio, C3-C8 cycloalkylthio, Ci-Cg alkylsulfinyl, Ci-Cg haloalkylsulfinyl, Ci-Cg alkylsulfonyl, Ci-Cg haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C2-Cg alkylthioalkyl or C2-Cg haloalkylthioalkyl;

Z is O;

R ² is halogen, C1-C4 alkyl or C 1-C4 haloalkyl;

each R ³ is independently halogen, cyano, CHO, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C 1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-Cg alkylcarbonyl, C2-Cg

haloalkylcarbonyl, C2-Cg alkoxycarbonyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-Cg alkoxyalkyl, C2-Cg haloalkoxyalkyl, C2-Cg cyanoalkyl or -SO _n R ¹⁴ ; and m is 0, 1 or 2.

Embodiment PB. A compound of Embodiment PA wherein

A is H ₂ , O or N(OR ⁵ );

R ¹ is C _x -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C _x -C ₆ haloalkyl, C ₂ -C ₆

haloalkenyl, C2-Cg haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, Ci-Cg alkoxy, C3-C6 alkenyloxy, C3-C6 alkynyloxy, Ci-Cg haloalkoxy, C3-C6 haloalkenyloxy, C3-C6 haloalkynyloxy or C3-C6 cycloalkoxy;

R ² is halogen or C1-C4 alkyl;

each R ³ is independently halogen, cyano, C1-C4 alkyl or C 1-C4 haloalkyl;

R ⁵ is H, C!-C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C!-C ₆ haloalkyl, C ₂ -C ₆

haloalkenyl, C2-Cg haloalkynyl, C2-Cg alkoxyalkyl, C2-Cg haloalkoxyalkyl, C2-Cg cyanoalkyl, C3-C7 cyanoalkoxyalkyl, C2-Cg alkylthioalkyl or C2-Cg haloalkylthioalkyl; and

m is 0 or 1.

Embodiment PC. A compound of Embodiment PB wherein

A is O or N(OR ⁵ );

R ¹ is Ci-Cg alkoxy, C3-C6 alkenyloxy, C3-C6 alkynyloxy, Ci-Cg haloalkoxy, C3-C6 haloalkenyloxy, C3-C6 haloalkynyloxy or C3-C6 cycloalkoxy;

R ² is halogen or CH ₃ ;

R ³ is independently halogen or cyano; and

R ⁵ is C!-C ₆ alkyl, or - haloalkyl.

Embodiment PD. A compound of Embodiment PC wherein

A is O;

R ² is halogen; and

each R ³ is independently halogen.

Specific embodiments include compounds of Formula 1 selected from the group consisting of:

3,3,3-trifluoropropyl 2-chloro-6-[(5-chloro-2-pyrimidinyl)oxy]benzoate (Compound 15),

3.3.3- trifluoro-l-methylpropyl 2-bromo-6-[(5-chloro-2-pyrimidinyl)oxy]benzoate (Compound 16),

propyl 2-bromo-6-[(5-chloro-2-pyrimidinyl)oxy]benzoate (Compound 13),

4.4.4- trifluorobutyl 2-bromo-6-[(5-chloro-2-pyrimidinyl)oxy]benzoate (Compound 20),

2- propen-l-yl 2-bromo-6-[(5-chloro-2-pyrimidinyl)oxy]benzoate (Compound 22),

3- buten-l-yl 2-bromo-6-[(5-chloro-2-pyrimidinyl)oxy]benzoate (Compound 21), 2,2,3,3,3-pentafluoropropyl 2-bromo-6-[(5-chloro-2-pyrimidinyl)oxy]benzoate (Compound 23), and

3,3,3-trifluoropropyl 2-bromo-6-[(5-chloro-2-pyrimidinyl)oxy]benzoate (Compound 26).

This invention also relates to a method for controlling undesired vegetation comprising applying to the locus of the vegetation herbicidally effective amounts of the compounds of the invention (e.g., as a composition described herein). Of note as embodiments relating to methods of use are those involving the compounds of embodiments described above. Compounds of the invention are particularly useful for selective control of weeds in crops such as wheat, barley, maize, soybean, sunflower, cotton, oilseed rape and rice, and specialty crops such as sugarcane, citrus, fruit and nut crops.

Also noteworthy as embodiments are herbicidal compositions of the present invention comprising the compounds of embodiments described above.

This invention also includes a herbicidal mixture comprising (a) a compound selected from Formula 1, N-oxides, and salts thereof, and (b) at least one additional active ingredient selected from (bl) photosystem II inhibitors, (b2) acetohydroxy acid synthase (AHAS) inhibitors, (b3) acetyl-CoA carboxylase (ACCase) inhibitors, (b4) auxin mimics, (b5) 5 -enol-pyruvylshikimate-3 -phosphate (EPSP) synthase inhibitors, (b6) photosystem I electron diverters, (b7) protoporphyrinogen oxidase (PPO) inhibitors, (b8) glutamine synthetase (GS) inhibitors, (b9) very long chain fatty acid (VLCFA) elongase inhibitors, (blO) auxin transport inhibitors, (bl l) phytoene desaturase (PDS) inhibitors, (bl2) 4-hydroxyphenyl-pyruvate di oxygenase (HPPD) inhibitors, (bl3) homogentisate solenesyltransererase (HST) inhibitors, (bl4) cellulose biosynthesis inhibitors, (bl5) other herbicides including mitotic disruptors, organic arsenicals, asulam, bromobutide, cinmethylin, cumyluron, dazomet, difenzoquat, dymron, etobenzanid, flurenol, fosamine, fosamine-ammonium, hydantocidin, metam, methyldymron, oleic acid, oxaziclomefone, pelargonic acid and pyributicarb, and (bl6) herbicide safeners; and salts of compounds of (bl) through (bl6). "Photosystem II inhibitors" (bl) are chemical compounds that bind to the D-l protein at the Qg-binding niche and thus block electron transport from to Q _Q in the chloroplast thylakoid membranes. The 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 cellular destruction. The Qg-binding niche has three different binding sites: binding site A binds the triazines such as atrazine, triazinones such as hexazinone, and uracils such as bromacil, binding site B binds the phenylureas such as diuron, and 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, bromofenoxim, bromoxynil, chlorbromuron, chloridazon, chlorotoluron, chloroxuron, cumyluron, cyanazine, daimuron, desmedipham, desmetryn, dimefuron, dimethametryn, diuron, ethidimuron, fenuron, fluometuron, hexazinone, ioxynil, isoproturon, isouron, lenacil, linuron, metamitron, methabenzthiazuron, metobromuron, metoxuron, metribuzin, monolinuron, neburon, pentanochlor, phenmedipham, prometon, prometryn, propanil, propazine, pyridafol, pyridate, siduron, simazine, simetryn, tebuthiuron, terbacil, terbumeton, terbuthylazine, terbutryn and trietazine.

"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 the 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, cloransulam-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, diclosulam, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone-sodium, flumetsulam, flupyrsulfuron-methyl, flupyrsulfuron- sodium, foramsulfuron, halosulfuron-methyl, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron-methyl (including sodium salt), iofensulfuron (2-iodo-N-[[(4-methoxy-6-methyl-l,3,5-triazin-2- yl)amino]carbonyl]benzenesulfonamide), mesosulfuron-methyl, metazosulfuron (3-chloro-4- (5,6-dihydro-5-methyl-l,4,2-dioxazin-3-yl)-N-[[(4,6-dimethox y-2- pyrimidinyl)amino]carbonyl]-l -methyl- lH-pyrazole-5-sulfonamide), metosulam, metsulfuron-methyl, nicosulfuron, oxasulfuron, penoxsulam, primisulfuron-methyl, propoxycarbazone-sodium, propyri sulfur on (2-chloro-N-[[(4,6-dimethoxy-2- pyrimidinyl)amino]carbonyl]-6-propylimidazo[l,2-^]pyridazine -3-sulfonamide),

prosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrithiobac-sodium, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thiencarbazone, thifensulfuron-methyl, triafamone (N-[2-[(4,6-dimethoxy-l,3,5-triazin-2-yl)carbonyl]-6- fluorophenyl]- 1, 1-difluoro-N-methylmethanesulfonamide), triasulfuron, tribenuron-methyl, trifloxysulfuron (including sodium salt), triflusulfuron-methyl and tritosulfuron.

"ACCase inhibitors" (b3) are chemical compounds that inhibit the acetyl-CoA carboxylase enzyme, which is responsible for catalyzing an early step in lipid and fatty acid synthesis 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 back. 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, cyhal of op-butyl, dicl of op-methyl and fenoxaprop-P-ethyl.

Auxin is a plant hormone that regulates growth in many plant tissues. "Auxin mimics"

(b4) are chemical compounds mimicking the plant growth hormone auxin, thus 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 its sodium and potassium salts, aminopyralid, benazolin-ethyl, chloramben, clacyfos, 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-m ethyl (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-3-chloro-6-(4- chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxyl ate.

"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 plant foliage and translocated in the phloem to the growing points. Glyphosate is a relatively nonselective postemergence herbicide that belongs to this group. Glyphosate includes esters and salts such as ammonium, isopropylammonium, potassium, sodium (including sesquisodium) and trimesium (alternatively named sulfosate).

"Photosystem I electron diverters" (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 cell membrane integrity, so that cells and organelles "leak", leading to rapid leaf wilting and desiccation, and eventually to plant death. Examples of this second type of photosynthesis inhibitor include diquat and paraquat.

"PPO inhibitors" (b7) are chemical compounds that inhibit the enzyme protoporphyrinogen oxidase, quickly resulting in formation of highly reactive compounds in plants that rupture cell membranes, causing cell fluids to leak out. Examples of PPO inhibitors include acifluorfen-sodium, azafenidin, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, cinidon-ethyl, fluazolate, flufenpyr-ethyl, flumiclorac-pentyl, flumioxazin, fluoroglycofen-ethyl, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, trifludimoxazin (dihydro-l,5-dimehyl-6-thioxo-3-[2,2,7-trifluoro-3,4-dihydro -3-oxo-4-(2-propyn-l-yl)-2H- l,4-benzoxazin-6-yl]-l,3,5-triazine-2,4(lH,3H)-dione) and tiafenacil (methyl N-[2-[[2- chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl) -l(2H)-pyrimidinyl]-4- fluorophenyl]thio]-l-oxopropyl]-P-alaninate).

"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 probably occurs due to the combined effects of ammonia toxicity and deficiency of amino acids required for other metabolic processes. The GS inhibitors include glufosinate and its esters and salts such as glufosinate-ammonium and other phosphinothricin derivatives, glufosinate-P ((2S)-2-amino- 4-(hydroxymethylphosphinyl)butanoic acid) and bilanaphos.

"VLCFA elongase inhibitors" (b9) are herbicides having a wide variety of chemical structures, which inhibit the elongase. Elongase is one of the enzymes located in or near chloroplasts which are involved in biosynthesis of VLCFAs. In plants, very-long-chain fatty acids are the main constituents of hydrophobic polymers that prevent desiccation at the leaf surface and provide stability to pollen grains. Such herbicides include acetochlor, alachlor, anilofos, butachlor, cafenstrole, dimethachlor, dimethenamid, diphenamid, fenoxasulfone (3- [[(2,5-dichloro-4-ethoxyphenyl)methyl]sulfonyl]-4,5-dihydro- 5,5-dimethylisoxazole), fentrazamide, flufenacet, indanofan, mefenacet, metazachlor, metolachlor, naproanilide, napropamide, napropamide-M ((2R)-N,N-diethyl-2-(l-naphthalenyloxy)propanamide), pethoxamid, piperophos, pretilachlor, propachlor, propisochlor, pyroxasulfone, and thenylchlor, including resolved forms such as S-metolachlor and chloroacetamides and oxyacetamides.

"Auxin transport inhibitors" (blO) are chemical substances that inhibit auxin transport in plants, such as by binding with an auxin-carrier protein. Examples of auxin transport inhibitors include diflufenzopyr, naptalam (also known as N-(l-naphthyl)phthalamic acid and 2-[(l-naphthalenylamino)carbonyl]benzoic acid). "PDS inhibitors" (bl l) are chemical compounds that inhibit carotenoid biosynthesis pathway at the phytoene desaturase step. Examples of PDS inhibitors include beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone norflurzon and picolinafen.

"HPPD inhibitors" (bl2) are chemical substances that inhibit the biosynthesis of synthesis of 4-hydroxyphenyl-pyruvate dioxygenase. Examples of HPPD inhibitors include benzobicyclon, benzofenap, bicyclopyrone (4-hydroxy-3-[[2-[(2-methoxyethoxy)methyl]-6- (trifluoromethyl)-3-pyridinyl]carbonyl]bicyclo[3.2.1]oct-3-e n-2-one), fenquinotrione (2-[[8- chloro-3,4-dihydro-4-(4-methoxyphenyl)-3-oxo-2-quinoxalinyl] carbonyl]-l,3- cyclohexanedione), isoxachlortole, isoxaflutole, mesotrione, pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate (l-[[l-ethyl-4-[3-(2- methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoyl]-lH-pyrazo l-5-yl]oxy]ethyl methyl carbonate), topramezone, 5-chloro-3 -[(2-hydroxy-6-oxo- 1 -cyclohexen- 1 -yl)carbonyl]- 1 -(4- methoxyphenyl)-2(lH)-quinoxalinone, 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6- dimethyl-3 (2H)-pyridazinone, 4-(4-fluorophenyl)-6-[(2-hydroxy-6-oxo- 1 -cyclohexen- 1 - yl)carbonyl]-2-methyl-l,2,4-triazine-3,5(2H,4H)-dione, 5-[(2-hydroxy-6-oxo-l-cyclohexen-

1- yl)carbonyl]-2-(3-methoxyphenyl)-3-(3-methoxypropyl)-4(3H)-p yrimidinone, 2-methyl-N- (4-methyl-l,2,5-oxadiazol-3-yl)-3-(methylsulfinyl)-4-(triflu oromethyl)benzamide and 2- methyl-3-(methylsulfonyl)-N-(l -methyl- lH-tetrazol-5-yl)-4-(trifluoromethyl)benzamide.

"HST inhibitors" (bl3) disrupt a plant's ability to convert homogentisate to

2- methyl-6-solanyl-l,4-benzoquinone, thereby disrupting carotenoid biosynthesis. Examples of HST inhibitors include haloxydine, pyriclor, cyclopyrimorate (6-chloro-3-(2- cyclopropyl-6-methylphenoxy)-4-pyridazinyl 4-morpholinecarboxylate), 3-(2-chloro-3,6- difluorophenyl)-4-hy droxy- 1 -methyl- 1 , 5 -naphthyridin-2( lH)-one, 7-(3 , 5 -dichloro-4- pyridinyl)-5-(2,2-difluoroethyl)-8-hydroxypyrido[2,3-^]pyraz in-6(5H)-one and 4-(2,6- diethyl-4-methylphenyl)-5-hy droxy -2,6-dimethyl-3(2H)-pyridazinone.

HST inhibitors also include com ounds of Formulae A and B.

B

wherein Rdl is H, CI or CF ₃ ; R<*2 i _s H, CI or Br; R<*3 is H or CI; R ^d4 is H, CI or CF ₃ ; Rd5 i _s CH ₃ , CH ₂ CH ₃ or CH ₂ CHF ₂ ; and R ^d6 is OH, or and R ^el is H, F, CI, CH ₃ or CH ₂ CH ₃ ; Re ² is H or CF ₃ ; Re ³ is H, CH ₃ or CH ₂ CH ₃ ; Re ⁴ is H, F or Br; Re ⁵ is CI, CH ₃ , CF ₃ , OCF ₃ or CH ₂ CH ₃ ; R ^e6 is H, CH ₃ , CH ₂ CHF ₂ or C≡CH; R ^e7 is OH, -OC(=0)Et, or -OC(=0)-t-Bu; and A ^e8 is N or CH.

"Cellulose biosynthesis inhibitors" (bl4) inhibit the biosynthesis of cellulose in certain plants. They are most effective when applied preemergence or early postemergence on young or rapidly growing plants. Examples of cellulose biosynthesis inhibitors include chlorthiamid, dichlobenil, flupoxam, indaziflam (N ² -[(lR,2,S)-2,3-dihydro-2,6-dimethyl-lH- inden-l-yl]-6-(l-fluoroethyl)-l,3,5-triazine-2,4-diamine), isoxaben and triaziflam.

"Other herbicides" (bl5) include herbicides that act through a variety of different modes of action such as mitotic disruptors (e.g., flamprop-M-methyl and flamprop-M-isopropyl), organic arsenicals (e.g., DSMA, and MSMA), 7,8-dihydropteroate synthase inhibitors, chloroplast isoprenoid synthesis inhibitors and cell-wall biosynthesis inhibitors. Other herbicides include those herbicides having unknown modes of action or do not fall into a specific category listed in (bl) through (bl4) or act through a combination of modes of action listed above. Examples of other herbicides include aclonifen, asulam, amitrole, bromobutide, cinmethylin, clomazone, cumyluron, daimuron, difenzoquat, etobenzanid, fluometuron, flurenol, fosamine, fosamine-ammonium, dazomet, dymron, ipfencarbazone ( 1 -(2,4-dichlorophenyl)-N-(2,4-difluorophenyl)- 1 ,5-dihydro-N-( 1 - methylethyl)-5-oxo-4H-l,2,4-triazole-4-carboxamide), metam, methyldymron, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb and 5-[[(2,6-difluorophenyl)methoxy]methyl]- 4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)isoxazole.

"Herbicide safeners" (bl6) are substances added to a herbicide formulation to eliminate or reduce phytotoxic effects of the herbicide to certain crops. These compounds protect crops from injury by herbicides but typically do not prevent the herbicide from controlling undesired vegetation. Examples of herbicide safeners include but are not limited to benoxacor, cloquintocet-mexyl, cumyluron, cyometrinil, cyprosulfamide, daimuron, dichlormid, dicyclonon, dietholate, dimepiperate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate, methoxyphenone, naphthalic anhydride, oxabetrinil, N-(aminocarbonyl)-2-methylbenzenesulfonamide and N- (aminocarbonyl)-2-fluorobenzenesulfonamide, l-bromo-4-[(chloromethyl)sulfonyl]benzene, 2-(dichloromethyl)-2-methyl-l,3-dioxolane (MG 191), 4-(dichloroacetyl)-l-oxa- 4-azospiro[4.5]decane (MON 4660), 2,2-dichloro-l-(2,2,5-trimethyl-3-oxazolidinyl)- ethanone and 2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfony l]- benzamide.

An embodiment of the present invention is a herbicidal mixture comprising (a) a compound of Formula 1, and (b) at least one additional active ingredient selected from (b l) photosystem II inhibitors, (b2) acetohydroxy acid synthase (AHAS) inhibitors, (b4) auxin mimics, (b5) 5 -enol-pyruvylshikimate-3 -phosphate (EPSP) synthase inhibitors, (b7) protoporphyrinogen oxidase (PPO) inhibitors, (b9) very long chain fatty acid (VLCFA) elongase inhibitors and (bl2) 4-hydroxyphenyl-pyruvate dioxygenase (ffPPD) inhibitors.

The compounds of Formula 1 can be prepared by general methods known in the art of synthetic organic chemistry. One or more of the following methods and variations as described in Schemes 1-10 can be used to prepare the compounds of Formula 1. The definitions of (A, Z, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ^6a and R ^6b ) in the compounds of Formulae 1-17 below are as defined above in the Summary of the Invention unless otherwise noted. Compounds of Formulae la-lb are various subsets of the compounds of Formula 1, and all substituents for Formulae la-lb are as defined above for Formula 1 unless otherwise noted.

As shown in Scheme 1 a compound of Formula 1 can be prepared by nucleophilic substitution by heating a compound of Formula 2 in a suitable solvent, such as acetonitrile, tetrahydrofuran or N,N-dimethylformamide in the presence of a base such as potassium or cesium carbonate, with a compound of Formula 3 (wherein LG is halogen or SC^Me). The reaction is typically conducted at temperatures ranging from 20 to 110 °C.

Scheme 1

As shown in Scheme 2, compounds of Formula lb (wherein A is S) can be prepared by reacting compounds of Formula la (wherein A is A-3 and B is O) with a thionation reagent such as Lawesson's reagent, tetraphosphorus decasulfide or diphosphorus pentasulfide in a solvent such as tetrahydrofuran or toluene. Typically, the reaction is carried out at temperatures ranging from 0 to 115 °C.

Scheme 2

lb

As shown in Scheme 3, a compound of Formula 2a (wherein A is A-3, B is O and Z is O) can be prepared by deprotection of a compound of Formula 4 (wherein R ²⁰ is CH ₃ or C(=0)CH ₃ ) with a suitable deprotecting agent. Suitable methoxy (i.e. when R ²⁰ is CH ₃ ) deprotecting reagents such as BBr ₃ , AICI3 and HBr in acetic acid can be used in the presence of solvents such as toluene, dichloromethane and dichloroethane at a temperature of from - 80 to 120 °C. Suitable acetoxy (i.e. when R ²⁰ is C(=0)CH ₃ ) deprotecting agents include potassium carbonate in methanol or ammonium acetate in aqueous methanol at room temperature can be used as discussed in Das, et al., Tetrahedron 2003, 59, 1049-1054 and methods cited therein. Alternatively, a compound of Formula 4 can be combined with Amberlyst 15© in methanol (as discussed in Das, et al. Tet. Lett. 2003, 44, 5465-5468) or combined with sodium acetate in ethanol (as discussed in Narender, T., et al. Synthetic Communications 2009, 39(11), 1949-1956) to obtain a compound of Formula 2a. Other useful phenolic protecting groups suitable for use in preparing a compound of Formula 2a can be found in Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 4th ed.; Wiley: Hoboken, New Jersey, 1991.

Scheme 3

wherein R ^u is CH ₃ or COCH3

As shown in Scheme 4 compounds of Formula 5 (wherein R ^la is alkyl, alkenyl, or alkynyl) can be prepared by reaction of organometallic reagents such as organomagnesium or organolithium reagents of Formula 6 with amides of the Formula 7. This reaction is typically carried out in a solvent such as tetrahydrofuran or diethyl ether at temperatures ranging from -78 to 25 °C. To those skilled in the art, Amides such as Formula 7 are commonly referred to as a 'Weinreb Amide' and this type of transformation is commonly referred to as the 'Weinreb-Nahm ketone synthesis.' See Synthesis 2008, 23, 3707-3738 and references cited therein. Scheme 4

wherein R is CH3 or COCH3 and R is alkyl, alkenyl or alkynyl

As shown in Scheme 5 compounds of Formula 8 can be prepared by reaction of acids of Formula 9 with alkylamines, alcohols or thiols of Formula 10 (wherein R ^{1 5} is alkoxy, alkylthio or alkylamino) in the presence of a dehydrative coupling reagent such as propylphosphonic anhydride, dicyclohexylcarbodiimide, N-(3-dimethylaminopropyl)- jV-ethylcarbodiimide, N,jV-carbonyldiimidazole, 2-chloro-l,3-dimethylimidazolium chloride or 2-chloro-l-methylpyridinium iodide. Polymer-supported reagents, such as polymer- supported cyclohexylcarbodiimide, are also suitable. These reactions are typically run at temperatures ranging from 0-60 °C in a solvent such as dichloromethane, acetonitrile, N,N-dimethylformamide or ethyl acetate in the presence of a base such as triethylamine, N,N-diisopropylamine, or l,8-diazabicyclo[5.4.0]undec-7-ene. See Organic Process Research & Development 2009, 13, 900-906 for coupling conditions employing propylphosphonic anhydride.

Scheme 5

wherein R is CH3 or COCH3 and R is alkoxy, thioalkyl or alkylamino

In Scheme 6 a compounds of Formula 11 (wherein R ^x is R ⁴ , OR ⁵ or R ^6a R ⁶ b) can readily be prepared by condensation of an organoamine, organohydroxylamine, or organohydrazine with a compound of Formula 8, typically in the presence of either an acid or base. Reactions are typically run in solvents such as methanol, ethanol, dichloromethane, or toluene at temperatures ranging from 20 - 110 °C. Suitable acids for the reactions include, but are not limited to, inorganic acids such as hydrochloric acids and organic acids such as acetic acid and trifluoroacetic acid. Suitable bases for the reaction include, but are not limited to, hydroxides such as sodium hydroxide, carbonates such as sodium and potassium carbonate, and organic bases such as sodium acetate and pyridine.

Scheme 6

11

wherein R ²⁰ is CH ₃ or COCH ₃ and R ^x is R ⁴ , OR ⁵ or NR*

As shown in Scheme 7 benzylic alcohols of Formula 12 can be prepared by reduction of aldehydes of Formula 13 by a wide variety of methods well known to those skilled in the art. Suitable reducing agents for the reaction include, but are not limited to, sodium borohydride, lithium aluminum hydride, and diisobutylaluminium hydride. A variety of solvents are also suitable for this reaction and include, but are not limited to, methanol, ethanol, and tetrahydrofuran with typically reaction temperatures ranging from -10 °C to 25 °C.

Scheme 7

12

13

,20

wherein R^" is CH ₃ or COCH ₃

As shown in Scheme 8 benzylic halides of Formula 14 (wherein X is CI, Br or I) can be prepared by substitution of alcohol with a halide on compounds of Formula 12 by a wide variety of methods well known to those skilled in the art. One such method employs thionyl chloride, optionally with N,N-dimethyl formamide, in solvents including, but not limited to dichloromethane, toluene, chloroform and no solvent at temperatures typically between 0 - 80 °C. Alternatively compounds of the Formula 14 can be prepared from benzyl alcohols of the Formula 12 employing a phosphorus reagent and a halide regent. A typical phosphorus reagent is triphenyl phosphine and halide reagents include, but are not limited to, carbon tetrahalide, N-halosuccinimide, dihalide, and tetrahalomethane. Solvents suitable for this reaction include, but are not limited to, dichloromethane, tetrahydrofuran, and acetonitrile and typical reaction temperatures range from -78 - 50 °C. This latter reaction is well known to those skilled in the art and is referred to as an 'Appel Reaction' . For examples see Smith, M. B.; March, J. March 's Advanced Organic Chemistry, 6 ^th ed., pages 576-580; John Wiley & Sons: Hoboken, New Jersey and references therein.

Scheme 8

12 14

wherein I ,T20" is CH ₃ or COCH ₃ and X is CI, Br or I

In Scheme 9 a benzylic heterateroatom containing compound of Formula 15 (wherein R ^lb is alkoxy, alkylthio or alkylamino) can readily be prepared by those skilled in the art by a displacement reaction with a compound of the Formula 14 using an appropriate heteroalkyl reagent of Formula 10 (alcohol, alkylamine, or thiol), typically in the presence of a base. Suitable solvents for the reaction include, but are not limited to, tetrahydrofuran, N,N-dimethylformamide, acetonitrile, toluene and dichloromethane. Suitable bases for the reaction include, but are not limited to, hydroxides such as sodium hydroxide and potassium hydroxide, hydride bases such as sodium hydride, carbonate bases such as sodium and potassium carbonate, and organic bases such as triethylamine and N,N-diethylisopropylamine. Additionally this reaction can be optionally substituted with an iodide, for example sodium iodide or tetrabutylammonium iodide.

heme 9

14 15

,20 l b .

wherein R is CH ₃ or COCH ₃ and R is alkoxy, alkylthio or alkylamino

As shown in Scheme 10 sulfone (n = 1) and sulfoxides (n = 2) of the Formula 16 can be readily prepared by the oxidation of a compound of Formula 17 (wherein A is A-l and R ²¹ is alkyl or haloalkyl) by a wide variety of methods well known to those skilled in the art. Suitable reagents for this reaction include but are not limited to, dihydrogen peroxide, 3-chloro-benzenecarboxylic acid, sodium periodate, and Oxone. Typical solvents for this reaction include dichloromethane, methanol, tetrahydrofuran, and acetic acid and a typical reaction temperature range between -78 to 50 °C. The sulfur is first oxidized to the sulfoxide (n = 1) followed by oxidation to the sulfone (n = 2). Careful monitoring reaction progress with well-established analytical methods (i.e. thin layer chromotagraphy, nuclear magnetic resonance, etc.) allows for selection of the sulfoxide or sulfone.

Scheme 10

20 21

wherein R is CH ₃ or COCH ₃ and R is alkyl or haloalkyl

In Scheme 11 a compound of Formula 18 can readily be prepared by alkylation of a compound of Formula 19. This can be accomplished using an appropriate alkylating reagent in the presence of an appropriate base. Suitable solvents for this reaction generally include polar solvents including but not limited to N,N-dimethylformamide, dimethyl sulfoxide, acetonitrile, or tetrahydrofuran. Suitable bases generally include but are not limited to sodium hydride, sodium amide, sodium hydroxide, and lithium diisopropyl amide. Reaction temperatures range from 0 °C to 100 °C as described in synthesis Example 5.

Scheme 11

19 18

As shown in Scheme 12 a compound of Formula 20 can be prepared through deoxygenation of a compound of Formula 21. One method utilizes a transition metal catalyst in the presence of a hydride source optionally in the presence of an acid utilizing a number of solvents including methanol and ethanol. A typical transition metal catalyst is palladium on carbon, and standard hydride sources include hydrogen gas, either at atmospheric or elevated pressure, or ammonium formate. Acids utilized for this reaction can include hydrochloric acid, sulfuric acid, and /?ara-toluenesulfonic acid. An example of this reaction can be found in J. Med. Chem. 1992, 35, 1818. A second method employs a hydride source in combination with an acid. Typical hydride sources include triethylsilane and sodium borohydride, in combination with Bronsted acids such as trifluoroacetic acid and acetic acid, or Lewis acids such as boron trifluoride etherate. The solvent for these reactions can be the acid alone or as a mixture with a number of other common solvents such as dichloromethane or acetonitrile. An example of this reaction can be found in US 2007/0003539 or in Step B of synthesis Example 6.

Scheme 12

As shown in Scheme 13 a compound of Formula 22 (where R ^la is alkyl, alenyl, or alkynyl) can be prepared by reaction of organometallic reagents such as organomagnesium or organolithium reagents with aldehydes of the Formula 23. This reaction is typically carried out in a solvent such as tetrahydrofuran or diethyl ether at temperatures ranging from -78 to 25 °C. An example of this reaction can be found in Synlett, 2016, 27, 789 or as described in Step A of synthesis Example 6.

Scheme 13

As shown in Scheme 14, compounds of Formula 25 can be prepared by a transition metal catalyzed coupling of a cyano group with a compound of Formula 24 (R ^3a = Br or I). Conditions for this reaction generally include a cyanide source and a copper catalyst or palladium catalyst with a co-catalyst. This reaction is typically carried out with a copper(I) halide in the presence of a ligand such as 2-(methylamino)ethylamine or trans-N,N'- dimethylcyclohexane-l,2-diamine with a metal cyanide salt. This reaction can be utilized in a range of polar aprotic solvents such as N,N-dimethylformamide, tetrahydrofuran, acetonitrile, N-methyl-2-pyrrolidone or toluene at temperatures ranging from 100 to 210 °C. This reaction is known to those skilled in the art as the Rosenmund-von Braun reaction. Similar conditions can be utilized with copper(I) cyanide with or without the presence of added ligand and cyanide source. The analogous coupling can be affected by using a palladium catalyst such as tetrakis(triphenylphosphine)palladium, palladium diacetate, or tris(dibenzylideneacetone)dipalladium with optional phosphine ligands and a co-catalyst such as zinc cyanide. These reactions can be carried out in a range of polar aprotic solvents such as N,N-dimethylformamide, N-methyl-2-pyrrolidone, acetonitrile and 1,4-dioxane at temperatures ranging from 80 to 150 °C. Alternatively a palladium co-catalyst such as copper(I) halide and a cyanide salt can be used in place of the zinc cyanide under similar conditions. An example of this reaction can be found in J. Am. Chem. Soc. 2003, 125, 2890 and as described in Step C of synthesis Example 6.

Scheme 14

Compounds of Formulae 24, 22 and 20 can readily be converted to a compound of Formula 1 using the methods discussed for Scheme 3 and Scheme 1; by deprotection of the PG group and subsequent alkylation with a compound of Formula 3. It is recognized by one skilled in the art that various functional groups can be converted into others to provide different compounds of Formula 1. For a valuable resource that illustrates the interconversion of functional groups in a simple and straightforward fashion, see Larock, R. C, Comprehensive Organic Transformations: A Guide to Functional Group Preparations, 2nd Ed., Wiley-VCH, New York, 1999. For example, intermediates for the preparation of compounds of Formula 1 may contain aromatic nitro groups, which can be reduced to amino groups, and then be converted via reactions well known in the art such as the Sandmeyer reaction, to various halides, providing compounds of Formula 1. The above reactions can also in many cases be performed in alternate order

It is recognized that some reagents and reaction conditions described above for preparing compounds of Formula 1 may not be compatible with certain functionalities present in the intermediates. In these instances, the incorporation of protection/deprotection sequences or functional group interconversions into the synthesis will aid in obtaining the desired products. The use and choice of the protecting groups will be apparent to one skilled in chemical synthesis (see, for example, Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991). One skilled in the art will recognize that, in some cases, after the introduction of a given reagent as depicted in any individual scheme, it may be necessary to perform additional routine synthetic steps not described in detail to complete the synthesis of compounds of Formula 1. One skilled in the art will also recognize that it may be necessary to perform a combination of the steps illustrated in the above schemes in an order other than that implied by the particular presented to prepare the compounds of Formula 1.

One skilled in the art will also recognize that compounds of Formula 1 and the intermediates described herein can be subjected to various electrophilic, nucleophilic, radical, organometallic, oxidation, and reduction reactions to add substituents or modify existing substituents.

Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. The following non-limiting Examples are illustrative of the invention. Steps in the following Examples illustrate a procedure for each step in an overall synthetic transformation, and the starting material for each step may not have necessarily 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. !H NMR spectra are reported in ppm downfield from tetramethylsilane; "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 isotopic abundance parent ion (M+l) formed by addition of H+ (molecular weight of 1) to the molecule, or (M-1) formed by the loss of H+ (molecular weight of 1) from the molecule, observed by using liquid chromatography coupled to a mass spectrometer (LCMS) using either atmospheric pressure chemical ionization (AP+) where "amu" stands for unified atomic mass units.

EXAMPLE 1

Preparation of 2-[(5-chloro-2-pyrimidinyl)oxy]-N-(2,2,2-trifluoroethyl)benz amide

(Compound 28)

Step A: Preparation of 2-methoxy-N-(2,2,2-trifluoroethyl)benzamide

A solution of 2,2,2-Trifluoroethylamine (1.28 g, 12.89 mmoles) and triethylamine (4.1 mL, 29.31 mmoles) in dichloromethane (30 mL) was cooled to 0 °C. The reaction mixture was treated with a solution of 2-methoxybenzoyl chloride (2.0 g, 11.72 mmoles) in in dichloromethane (8 mL) at a temperature below 5 °C. The reaction mixture was allowed to slowly warm to room temperature. De-ionized water was added and the mixture partitioned. The aqueous phase was extracted with dichloromethane. The combined organic phases were washed with IN HCl and saturated aqueous sodium chloride solution and dried with magnesium sulfate and concentrated under vacuum to a white solid. The solid was filtered from hexanes to obtain the title compound (2.24 g) as a solid.

¾ NMR (400 MHz, CDC1 ₃ ) δ 8.20 (d, 2H), 7.49 (t, 1H), 7.10 (t, 1H), 7.00 (d, 1H), 4.10 (q, 2H), 3.99 (s, 3H).

Step B: Preparation of 2-hydroxy-N-(2,2,2-trifluoroethyl)benzamide

A solution of 2-methoxy-N-(2,2,2-trifluoroethyl)benzamide (i.e. the product of Step A) (1.0 g, 4.28 mmoles) in anhydrous dichloromethane (20 mL) was cooled with an ice-water bath to 0 °C. The solution was treated with 1 M boron tribromide solution (4.72 mL, 4.72 mmoles) in dichloromethane dropwise and stirred for 3 hours. The reaction mixture was then poured into ice-water and partitioned. The aqueous phase was extracted with dichloromethane and then ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried with magnesium sulfate and concentrated under vacuum to a solid. The solid was filtered from hexanes to obtain the title compound (475 mg) as a solid.

!H NMR (400 MHz, CDC1 ₃ ) δ 7.44 (t, 1H), 7.40 (d, 1H), 7.01 (d, 1H), 6.89 (t, 1H), 6.53 (bs, 1H), 4.13 (m,2 H).

Step C: Preparation of 2-[(5-chloro-2-pyrimidinyl)oxy]-N-(2,2,2-trifluoroethyl)- benzamide

To a solution of 2-hydroxy-N-(2,2,2-trifluoroethyl)benzamide (i.e. the product of Step B) (100 mg, 0.456 mmoles) in acetonitrile (3 mL) was added 2,5-dichloropyrimidine (71 mg, 0.48 mmoles) and potassium carbonate (190 mg, 1.37 mmoles). The reaction mixture was heated to 80 °C for 12 hours. The reaction was partitioned between water and ethyl acetate, the organic phase was separated, dried with magnesium sulfate, and concentrated under vacuum. The residue was purified by chromatography on silica gel with a 5 gram Bond elut column, eluting with 20% ethyl acetate/hexanes to afford the title compound, a compound of the present invention, as an oil (0.30 g).

!H NMR (400 MHz, CDC1 ₃ ) δ 8.30 (s, 2H), 7.65 (d, 1H), 7.48 (t, 1H), 7.31 (t, 1H), 7.21 (bs, 1H), 7.00 (d, 1H), 4.75 (q, 2H). EXAMPLE 2

Preparation of 3-buten-l-yl 2-bromo-6-[(5-chloro-2-pyrimidinyl)oxy]benzoate

(Compound 21)

Step A: Preparation of 3-butenyl 2-bromo-6-hydroxybenzoate

To a stirred solution of 2-bromo-6-hydroxybenzoic acid (0.200 g, 0.921 mmol) in dry dichloromethane (3 mL) was added oxalyl chloride (94.8 μΐ., 1.11 mml) and 2 drops of N,N'-dimethylformamide. The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was then concentrated under vacuum and the residue was dissolved in dry dichloromethane (3 mL) and treated with 3-buten-l-ol (86.9 μΕ, 1.01 mmol) and 3 drops of triethylamine. The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated under vacuum onto Celite ^® diatomaceous earth filter aid and purified by column chromatography on silica gel, eluting with 0 to 20% ethyl acetate in hexanes to afford the title compound (0.117 g).

¾ NMR (500 MHz, CDC1 ₃ ) δ 10.96 (s, 1H), 7.24-7.17 (m, 2H), 6.98-6.93 (m, 1H), 5.95- 5.87 (m, 1H), 5.22-5.18 (m, 1H), 5.15-5.12 (m, 1H), 4.47 (t, 2H), 2.62-2.57 (m, 2H).

Step B: Preparation of 3-buten-l-yl 2-bromo-6[(5-chloro-2-pyrimidinyl)oxy]benzoate

To a stirred solution of 3-butenyl 2-bromo-6-hydroxybenzoate (i.e. the product of Step A) (0.117 g, 0.431 mmol) and 5-chloro-2-(methylsulfonyl)-pyrimidine (i.e. 5-chloro-2- methylsulfonylpyrimidine) (99.8 mg, 0.518 mmol) in N,N'-dimethylformamide (2 mL) was added potassium carbonate (85.9 mg, 0.646 mmol). The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was then filtered through a pad of Celite ^® diatomaceous earth filter aid and the filtrate was concentrated under vacuum. The crude residue was purified by column chromatography on silica gel, eluting with 0 to 30% ethyl acetate in hexanes to afford the title compound, a compound of the present invention, as a solid (0.104 g).

!H MR (500 MHz, CDC1 ₃ ) δ 8.48 (s, 2H), 7.53 (dd, 1H), 7.35 (t, 1H), 7.17 (dd, 1H), 5.75- 5.65 (m, 1H), 5.11-4.99 (m, 2H), 4.29 (t, 2H), 2.39-2.34 (m, 2H).

EXAMPLE 3

Preparation of 3,3,3-trifluoropropyl 2-bromo-6-[(5-chloro-2-pyrimidinyl)oxy]benzoate

(Compound 26)

Step A: Preparation of 3,3,3-trifluoropropyl 2-bromo-6-hydroxybenzoate

To a stirred solution of 2-bromo-6-hydroxybenzoic acid (0.500 g, 2.30 mmol) and molecular sieves in 3,3,3-trifluoropropan-l-ol (15 mL) was added concentrated sulfuric acid (0.300 mL). The reaction mixture was heated at 78 °C for 24 hours. The reaction mixture was cooled to room temperature and filtered through a small pad of Celite ^® diatomaceous earth filter aid. The filtrate was diluted with ethyl acetate and washed with water, and saturated aqueous sodium chloride solution. The organic phase was separated, dried over magnesium sulfate and concentrated under vacuum. The crude material was purified by column chromatography on silica gel, eluting with 0 to 20% ethyl acetate in hexanes to afford the title compound (0.268 g).

!H MR (500 MHz, CDC1 ₃ ) δ 10.79 (s, 1H), 7.26-7.20 (m, 2H), 7.00-6.94 (m, 1H), 4.63 (t, 2H), 2.70 (m, 2H).

Step B: Preparation of 3,3,3-trifluoropropyl 2-bromo-6-[(5-chloro-2-pyrimidinyl)- oxy]benzoate

To a stirred solution of 3,3,3-trifluoropropyl 2-bromo-6-hydroxybenzoate (i.e. the product of Step A) (0.124 g, 0.396 mmol) and 5-chloro-2-(methylsulfonyl)-pyrimidine (i.e. 5-chloro-2-methylsulfonylpyrimidine) (95.1 mg, 0.475 mmol) in N,N'-dimethylformamide (2 mL) was added potassium carbonate (82.1 mg, 0.594 mmol). The reaction was stirred at room temperature for 18 hours. The reaction mixture was filtered through a pad of Celite ^® diatomaceous earth filter aid and filtrate was concentrated under vacuum. The crude material was purified by column chromatography on silica gel, eluting with 0 to 30% ethyl acetate in hexanes to afford the title compound, a compound of the present invention, as a solid (55.0 mg).

!H MR (500 MHz, CDCI3) δ 8.49 (s, 2H), 7.54 (dd, 1H), 7.38 (t, 1H), 7.20 (dd, 1H), 4.46 (t, 2H), 2.50 (m, 2H).

EXAMPLE 4

Preparation of l-[2-chloro-6-[(5-chloro-2-pyrimidinyl)oxy]phenyl]-4,4,4-tri fluoro-l- butanone (Compound 107)

Step A: Preparation of 2-chloro-6-methoxy-a-(3,3,3-trifluoropropyl)benzenemethanol

A reaction flask was charged with 1.92 g (79.18 mmol) of magnesium, a catalytic amount of iodine, and 50 mL of diethyl ether. The mixture was heated to reflux and 1, 1,1- trifluoro-3-iodo-propane (10.64 g, 47.51 mmol) was added over 30 min. The mixture was allowed to cool to room temperature and transferred to a second reaction flask charged with 2-chloro-6-methoxy-benzaldehyde (6.75 g, 39.59 mmol) and 75 mL of tetrahydrofuran at -78 °C. The reaction mixture was allowed to warm to room temperature, quenched with 1 N hydrochloric acid, and partitioned between diethyl ether and brine. The organic phase was dried over MgS0 ₄ , filtered, and concentrated to provide 9.4 g of crude product that was used in the subsequent step without purification.

Step B: Preparation of l-(2-chloro-6-methoxyphenyl)-4,4,4-trifluoro-l-butanone

To a solution of 2-chloro-6-methoxy-a-(3,3,3-trifluoropropyl)benzenemethanol (i.e. the crude material obtained in Step A, 9.4 g) in 175 mL of acetone was added 15.7 mL (42 mmol) of 2.64 M Jones reagent over 15 min. The reaction mixture was stirred for an additional 30 min., quenched with 0.5 mL of isopropanol, and partitioned between diethyl ether and water. The organic phase was dried over MgSC^, filtered, and concentrated. The crude material was purified by silica gel chromatography eluting with a hexane:ethyl acetate gradient to provide 7.0 g of the title compound.

¾ NMR (CDCI3) δ 7.32-7.24 (m, 1H), 7.00 (d, 1H), 6.84 (d, 1H), 3.82 (s, 3H), 3.09-3.01 (m, 2H), 2.64-2.51 (m, 2H).

Step C: Preparation of l-(2-chloro-6-hydroxyphenyl)-4,4,4-trifluoro-l-butanone

To a solution of l-(2-chloro-6-methoxyphenyl)-4,4,4-trifluoro-l-butanone (i.e. the product from Step B, 3.5 g, 13.2 mmol) of in 100 mL of dichloromethane was added boron tribromide (1.0 M in dichloromethane, 15.79 mL) at 0 °C. The reaction solution was stirred for 2 h while warming to room temperature, which was then poured into ice cold dilute aqueous hydrochloric acid, and extracted with dichloromethane. The organic phase was dried over MgS0 ₄ , filtered, and concentrated. The crude material was purified by silica gel chromatography eluting with a gradient of hexanes/ethyl acetate to provide 2.6 g of the title compound.

¾ NMR (CDCI3) δ 11.88 (s, 1H), 7.35-7.30 (m, 1H), 7.01-6.98 (m, 1H), 6.96-6.92 (m, 1H), 3.55-3.49 (m, 2H), 2.65-2.53 (m, 2H).

Step D: Preparation of l-[2-chloro-6-[(5-chloro-2-pyrimidinyl)oxy]phenyl]-4,4,4- trifluoro- 1 -butanone

A reaction flask was charged with l-(2-chloro-6-hydroxyphenyl)-4,4,4-trifluoro-l- butanone (i.e. the product obtained in Step C, 2.6 g, 10.3 mmol), 5-chloro-2- (methylsulfonyl)-pyrimidine (2.7 g, 14.0 mmol), potassium carbonate (1.7 g, 12.36 mmol), and 50 mL of isopropanol. The reaction mixture was heated to 50 °C for 1 h, poured into dilute ice cold aqueous hydrochloric acid, and extracted with diethyl ether repeatedly. The combined organic extracts were washed with brine, dried over MgS0 ₄ , filtered, and concentrated. The crude material was purified by silica gel chromatography eluting with a gradient of hexanes/ethyl acetate to provide 3.0 g of the title compound, a compound of the invention.

¾ NMR (CDCI3) δ 8.49 (s, 2H), 7.45-7.40 (m, 1H), 7.37-7.33 (m, 1H), 7.15-7.11 (m, 1H), 3.14-3.08 (m, 2H), 2.57-2.46 (m, 2H).

EXAMPLE 5

Preparation of 2-[(5-chloro-2-pyrmidinyl)oxy]-a-pentylbenzeneacetonitrile (Compound 141) Step A: Preparation of 2-methoxy-a-pentylbenzeneacetonitrile

To a solution of 2-methoxy-benzeneacetonitrile (500 mg, 3.39 mmol) in dimethylsulfoxide (5 mL) was added aqueous sodium hydroxide (50%, 0.75 mL) followed by 1-bromopentane (559 mg, 0.458 mL, 3.76 mmol) and the reaction mixture was stirred at ambient temperature for 18 h. The reaction mixture was partitioned between ethyl acetate and water, the organic phase was washed with water (3 ^χ ). The organic phase was dried over MgSC"4 and concentrated under vacuum. The resulting residue was purified by chromatography on silica gel eluting with a gradient of 0 to 50% ethyl acetate in hexanes to afford the desired product in quantitative yield.

¾ NMR (500 MHz, CDC1 ₃ ) δ 7.38-7.41 (m, 1H), 7.27-7.31 (m, 1H), 6.96-7.01 (m, 1H), 6.87-6.91 (m, 1H), 4.15-4.20 (m, 1H), 3.85 (s, 3H), 1.77-1.90 (m, 2H), 1.41-1.58 (m, 2H), 1.27-1.37 (m, 4H), 0.84-0.94 (m, 3H).

Step B: Preparation of 2-hydroxy-a-pentylbenzeneacetonitrile

To a solution of 2-methoxy-a-pentylbenzeneacetonitrile (i.e. the product of Step A, 440 mg, 2.02 mmol) in dichloromethane (10 mL) at 0 °C was added boron tribromide (1.0 M in dichloromethane, 10 mL, 10 mmol) and the reaction was allowed to warm to room temperature over 18 h. The reaction mixture was quenched with a saturated solution of sodium carbonate, the phases were separated and the organic layer was dried over MgS0 ₄ . The solvent was removed under vacuum and purified by chromatography on silica gel, eluting with a gradient of 0 to 50% ethyl acetate in hexanes to afford the desired product (232 mg)

¾ NMR (500 MHz, CDC1 ₃ ) δ 7.35-7.39 (m, 1H), 7.15-7.20 (m, 1H), 6.93-6.98 (m, 1H), 6.76-6.79 (m, 1H), 5.28-5.40 (bs, 1H), 4.14-4.20 (m, 1H), 1.84-1.93 (m, 2H), 1.42-1.58 (m, 2H), 1.25-1.38 (m, 4H), 0.85-0.91 (m, 3H).

Step C: Preparation of 2-[(5-chloro-2-pyrmidinyl)oxy]-a-pentylbenzeneacetonitrile

To a solution of 2-hydroxy-a-pentylbenzeneacetonitrile (208 mg, 1.02 mmol) in N,N'-dimethylformamide (2.0 mL) was added potassium carbonate (169 mg, 1.22 mmol) followed by 5-chloro-2-(methylsulfonyl)-pyrimidine (137 mg, 1.07 mmol) and the reaction was heated to 35 °C for 5 h. The reaction was partitioned between ethyl acetate and water. The organic phase was washed with water (3 ^χ ), followed by drying over MgS0 ₄ and concentrating. The resulting residue was purified by chromatography on silica gel eluting with a gradient of 0 to 30% ethyl acetate in hexanes to afford the title product, a compound of the invention (171 mg).

¾ NMR (500 MHz, CDC1 ₃ ) δ 8.51 (s, 2H), 7.56-7.58 (m, 1H), 7.38-7.42 (m, 1H), 7.31- 7.35 (m, 1H), 7.12-7.15 (m, 1H), 3.99-4.03 (m, 1H), 1.80-1.96 (m, 2H), 1.36-1.55 (m, 2H), 1.20-1.28 (m, 4H), 0.81-0.87 (m, 3H).

EXAMPLE 6

Preparation of 3-[(5-chloro-2-pyrimidinyl)oxy]-2-(5,5,5-trifluoropentyl)ben zonitrile

(Compound 73)

Step A: Preparation of 2-bromo-6-methoxy-a-(4,4,4-trifluorobutyl)benzenemethanol

To magnesium metal shavings (0.254 g, 10.5 mmol, 1.5 eq.) in dry diethyl ether (2 mL) was added a crystal of iodine. The mixture was warmed to 35 °C and stirred for 15 min. To this mixture was added l-bromo-4,4,4-trifluorobutane (1.30 mL, 10.5 mmol, 1.5 eq.) over 30 min. The reaction mixture continued to stir at 35 °C until all the magnesium was consumed. The resulting Grignard reagent was taken up by syringe. In separate reaction vial 2-bromo-6-methoxy-benzaldehyde (1.50 g, 6.97 mmol, 1.0 eq.) was dissolved in dry tetrahydrofuran (20 mL) and cooled to 0 °C. The previously prepared Grignard reagent was added dropwise to the aldehyde. The reaction mixture was stirred at room temperature for 18 h. The reaction was quenched with 1 N hydrochloric acid and diluted with ethyl acetate. The organic layer was separated, dried and concentrated. The crude material was purified by column chromatography, eluting with a gradient of 0 to 20% ethyl acetate in hexanes to afford the desired product (2.15 g).

1H MR (500MHz, CDC1 ₃ ) δ 7.21-7.16 (m, 1H), 7.09 (t, 1H), 6.90-6.87 (m, 1H), 5.17-5.09 (m, 1H), 3.90 (s, 3H), 3.72 (d, 1H), 2.24-2.10 (m, 2H), 2.02-1.75 (m, 3H), 1.73-1.61 (m, 1H).

Step B: Preparation of l-bromo-3-methoxy-2-(5,5,5-trifluoropentyl)benzene

To a stirred solution of 2-bromo-6-methoxy-a-(4,4,4-trifluorobutyl)benzenemethanol (i.e. the product of Step A, 2.15 g, 6.58 mmol, 1.0 eq.) in dry dichloromethane (22 mL) was added triethylsilane (4.20 mL, 26.3 mmol, 4.0 eq.). After stirring for 15 min. trifluoroacetic acid (2.01 mL, 26.3 mmol, 4.0 eq.) was added and the reaction was heated to 40 °C. After 2 h, another 4.0 eq. of trifluoroacetic acid was added and the reaction mixture was stirred at 40 °C for another 18 h. The reaction was cooled to room temperature and concentrated onto Celite ^® diatomaceous earth filter aid for purification by column chromatography, eluting with a gradient of 0 to 10% ethyl acetate in hexanes to afford the desired product (1.82 g). 1H MR (500MHz, CDC1 ₃ ) δ 7.20-7.12 (m, 1H), 7.07-7.00 (m, 1H), 6.81-6.78 (m, 1H), 3.81 (s, 3H), 2.85-2.78 (m, 2H), 2.20-2.07 (m, 2H), 1.69-1.55 (m, 4H)

Step C: Preparation of 3-methoxy-2-(5,5,5-trifluoropentyl)benzonitrile

A solution of l-bromo-3-methoxy-2-(5,5,5-trifluoropentyl)benzene (i.e. the product of Step B, 1.82 g, 5.86 mmol, 1.0 eq.) in N,N-dimethylformamide (20 mL) was deoxygenated by bubbling N ₂ through the reaction mixture for -10 min. To this mixture was added copper(I) cyanide (1.57 g, 17.6 mmol, 3.0 eq.). The reaction was refluxed at 160 °C under nitrogen for 18 h. The reaction was cooled to ambient temperature and filtered through a pad of Celite ^® diatomaceous earth filter aid. The filtrate was diluted with ethyl acetate and washed several times with water, then once with brine. The organic layer was dried and concentrated in vacuo. The crude material was purified by column chromatography, eluting with 0 to 30%) ethyl acetate in hexanes to afford the desired product (1.38 g).

1H MR (500MHz, CDC1 ₃ ) δ 7.29-7.24 (m, 1H), 7.22-7.19 (m, 1H), 7.08-7.04 (m, 1H), 3.86 (s, 3H), 2.94-2.82 (m, 2H), 2.24-2.07 (m, 2H), 1.75-1.60 (m, 4H).

Step D: Preparation of 3-hydroxy-2-(5,5,5-trifluoropentyl)benzonitrile

A solution of 3-methoxy-2-(5,5,5-trifluoropentyl)benzonitrile (i.e. the product of Step C, 1.38 g, 5.36 mmol, 1.0 eq.) in dichloroethane (17 mL) was treated with boron tribromide (1.0 M in dichloromethane, 10.7 mL, 10.7 mmol, 2.0 eq.). The reaction mixture was heated to 60 °C for 18 h. The reaction was cooled to ambient temperature and quenched with saturated aqueous sodium bicarbonate. The organic phase was separated, dried and concentrated onto Celite ^® diatomaceous earth filter aid for purification by column chromatography, eluting with a gradient of 0 to 30% ethyl acetate in hexanes to afford the desired product (1.16 g).

1H MR (500MHz, CDC1 ₃ ) δ 7.25-7.21 (m, 1H), 7.19-7.15 (m, 1H), 6.98-6.95 (m, 1H), 5.05-5.01 (m, 1H), 2.92-2.86 (m, 2H), 2.20-2.08 (m, 2H), 1.78-1.62 (m, 4H).

Step E: Preparation of 3 - [(5 -chloro-2-pyrimidinyl)oxy ]-2-(5 ,5,5- trifluoropentyl)benzonitrile

A mixture of 3-hydroxy-2-(5,5,5-trifluoropentyl)benzonitrile (i.e. the product of Step D, 1.16 g, 4.79 mmol, 1.0 eq.), 5-chloro-2-(methylsulfonyl)-pyrimidine (1.11 g, 5.75 mmol, 1.2 quiv) and potassium carbonate (0.993 g, 7.18 mmol, 1.5 eq.) in N,N-dimethylformamide (16 mL) was stirred at room temperature for 18 h. The reaction mixture was heavily diluted with ethyl acetate and washed several times with water, then once with brine. The organic phase was dried and concentrated onto Celite ^® diatomaceous filter aid for purification by column chromatography, eluting with a gradient of 0 to 30% ethyl acetate in hexanes to afford the desired product (1.65 g).

1H MR (500MHz, CDC1 ₃ ) δ 8.52-8.48 (m, 2H), 7.61-7.56 (m, 1H), 7.42-7.36 (m, 1H), 7.35-7.31 (m, 1H), 2.87-2.78 (m, 2H), 2.16-2.00 (m, 2H), 1.74-1.64 (m, 2H), 1.63-1.54 (m, 2H).

By the procedures described herein together with methods known in the art, the following compounds of Tables 1 to 585 can be prepared. The following abbreviations are used in the Tables which follow: t means tertiary, s means secondary, n means normal, / ^' means iso, c means cyclo, Me means methyl, Et means ethyl, Pr means propyl, Bu means butyl, / ^' -Pr means isopropyl, Bu means butyl, c-Pr cyclopropyl, Ph means phenyl, OMe means methoxy, OEt means ethoxy, SMe means methylthio, HMe methylamino, -CN means cyano, S(0)Me means methylsulfinyl, and S(0) ₂ Me means methyl sulfonyl.

R ² = F, (R ³ ) _m = 3-F, Z = O and A = A-3 A

Rl R

butyl 3 ,3 ,4,4,4-pentafluorobutoxy tert-butyl 2,2,3 ,3 ,3 -pentafluoropropoxy etiiyl 3 ,3 ,4,4-tetrafluorobutoxy hexyl 2,2,3 ,3 -tetrafluoropropoxy isobutyl 3 ,3 ,3 -trichloropropoxy isopentyl 4,4,4-trifluorobutoxy metiiyl 2,2,2-trifluoroethoxy pentyl 6,6,6-trifluorohexoxy propyl 4,4,4-trifluoro-2-methyl-butoxy benzyl 3 ,3 ,3 -trifluoropropoxy allyl 4-bromobut-3 -ynoxy 3-buten-l-yl 4-chlorobut-3 -ynoxy

3- methyl-2-buten-l-yl 3 -chloroprop-2 -ynoxy 3 -methy 1-3 -buten- 1 -y 1 4,4-difluorobut-2 -ynoxy

4- methy 1-3 -penten- 1 -yl 5,5, 5-trifluoropent-2 -ynoxy

3-penten-l-yl 5,5,5-trifluoropent-3-ynoxy 3-buryn-l-yl cyclobutylmethoxy

4-methyl-2-pentyn- 1 -yl cyclohexoxy

3- pentyn-l-yl cyclopentoxy

2- propyn-l-yl 2-cyclopropylethoxy 5-hexyn-l-yl cyclopropylmethoxy

4- pentyn-l-yl (2-bromo-2-chloro-cyclopropyl)methoxy

3- bromopropyl (2,2-dibromocyclopropyl)methoxy

The present disclosure also includes Tables 2 through 292. Each Table is constructed in the same manner as Table 1 above, except that the row heading in Table 1 (i.e. "R ² = F, (R ³ ) _m = 3-F, Z = O and A = A-3A") is replaced with the respective row heading shown below. For example, the first entry in Table 2 is a compound of Formula 1 wherein R ² is CI, (R ³ ) _m is 3-F, Z is O, A is A-3A and R ¹ is butyl. Tables 3 through 292 are constructed similarly.

Header Row Header Row

Table R ² (R ³ )m Z A Table R ² (R ³ )m Z A

2 CI 3-F 0 A-3A 147 F 5-Cl 0 A-3B

3 Br 3-F 0 A-3A 148 CI 5-Cl 0 A-3B

4 I 3-F 0 A-3A 149 Br 5-Cl 0 A-3B

5 CF ₃ 3-F 0 A-3A 150 I 5-Cl 0 A-3B Header Row Header Row

Table Z A Table R2 (R ³ )m Z A

6 0 A-3A 151 CF ₃ 5-Cl 0 A-3B

7 0 A-3A 152 OMe 5-Cl 0 A-3B

8 0 A-3A 153 Me 5-Cl 0 A-3B

9 0 A-3A 154 F 6-Cl 0 A-3B

10 0 A-3A 155 CI 6-Cl 0 A-3B

11 0 A-3A 156 Br 6-Cl 0 A-3B

12 0 A-3A 157 I 6-Cl 0 A-3B

13 0 A-3A 158 CF ₃ 6-Cl 0 A-3B

14 0 A-3A 159 OMe 6-Cl 0 A-3B

15 0 A-3A 160 Me 6-Cl 0 A-3B

16 0 A-3A 161 F 3 -Br, 4-F 0 A-3B

17 0 A-3A 162 CI 3 -Br, 4-F 0 A-3B

18 0 A-3A 163 Br 3 -Br, 4-F 0 A-3B

19 0 A-3A 164 I 3 -Br, 4-F 0 A-3B

20 0 A-3A 165 CF ₃ 3 -Br, 4-F 0 A-3B

21 0 A-3A 166 OMe 3 -Br, 4-F 0 A-3B

22 0 A-3A 167 Me 3 -Br, 4-F 0 A-3B

23 0 A-3A 168 F 3-F, 4-F 0 A-3B

24 0 A-3A 169 CI 3-F, 4-F 0 A-3B

25 0 A-3A 170 Br 3-F, 4-F 0 A-3B

26 0 A-3A 171 I 3-F, 4-F 0 A-3B

27 0 A-3A 172 CF ₃ 3-F, 4-F 0 A-3B

28 0 A-3A 173 OMe 3-F, 4-F 0 A-3B

29 0 A-3A 174 Me 3-F, 4-F 0 A-3B

30 0 A-3A 175 F 3 -CI, 4-F 0 A-3B

31 0 A-3A 176 CI 3 -CI, 4-F 0 A-3B

32 0 A-3A 177 Br 3 -CI, 4-F 0 A-3B

33 0 A-3A 178 I 3 -CI, 4-F 0 A-3B

34 0 A-3A 179 CF ₃ 3 -CI, 4-F 0 A-3B

35 0 A-3A 180 OMe 3 -CI, 4-F 0 A-3B

36 0 A-3A 181 Me 3 -CI, 4-F 0 A-3B

37 0 A-3A 182 F 3 -Br s A-3B

38 0 A-3A 183 CI 3 -Br s A-3B

39 0 A-3A 184 Br 3 -Br s A-3B

40 0 A-3A 185 I 3 -Br s A-3B

41 0 A-3A 186 CF ₃ 3 -Br s A-3B Header Row Header Row

Table Z A Table R2 (R ³ )m Z A

42 0 A-3A 187 OMe 3-Br s A-3B

43 0 A-3A 188 Me 3-Br s A-3B

44 0 A-3A 189 F 3 -CI s A-3B

45 0 A-3A 190 CI 3 -CI s A-3B

46 0 A-3A 191 Br 3 -CI s A-3B

47 0 A-3A 192 I 3 -CI s A-3B

48 0 A-3A 193 CF ₃ 3 -CI s A-3B

49 0 A-3A 194 OMe 3 -CI s A-3B

50 0 A-3A 195 Me 3 -CI s A-3B

51 0 A-3A 196 CI 3-F 0 A-l

52 0 A-3A 197 Br 3-F 0 A-l

53 0 A-3A 198 I 3-F 0 A-l

54 0 A-3A 199 CF ₃ 3-F 0 A-l

55 0 A-3A 200 OMe 3-F 0 A-l

56 0 A-3A 201 Me 3-F 0 A-l

57 0 A-3A 202 F 3 -CI 0 A-l

58 0 A-3A 203 CI 3 -CI 0 A-l

59 0 A-3A 204 Br 3 -CI 0 A-l

60 0 A-3A 205 I 3 -CI 0 A-l

61 0 A-3A 206 CF ₃ 3 -CI 0 A-l

62 0 A-3A 207 OMe 3 -CI 0 A-l

63 0 A-3A 208 Me 3 -CI 0 A-l

64 0 A-3A 209 F 3-Br 0 A-l

65 0 A-3A 210 CI 3-Br 0 A-l

66 0 A-3A 211 Br 3-Br 0 A-l

67 0 A-3A 212 I 3-Br 0 A-l

68 0 A-3A 213 CF ₃ 3-Br 0 A-l

69 0 A-3A 214 OMe 3-Br 0 A-l

70 0 A-3A 215 Me 3-Br 0 A-l

71 0 A-3A 216 F 3-1 0 A-l

72 0 A-3A 217 CI 3-1 0 A-l

73 0 A-3A 218 Br 3-1 0 A-l

74 0 A-3A 219 I 3-1 0 A-l

75 0 A-3A 220 CF ₃ 3-1 0 A-l

76 0 A-3A 221 OMe 3-1 0 A-l

77 0 A-3A 222 Me 3-1 0 A-l Header Row Header Row

Table Z A Table R2 (R ³ )m Z A

78 0 A-3A 223 F 3-CN 0 A-l

79 0 A-3A 224 CI 3-CN 0 A-l

80 0 A-3A 225 Br 3-CN 0 A-l

81 0 A-3A 226 I 3-CN 0 A-l

82 0 A-3A 227 CF ₃ 3-CN 0 A-l

83 0 A-3A 228 OMe 3-CN 0 A-l

84 0 A-3A 229 Me 3-CN 0 A-l

85 s A-3A 230 F 3-CF ₃ 0 A-l

86 s A-3A 231 CI 3-CF ₃ 0 A-l

87 s A-3A 232 Br 3-CF ₃ 0 A-l

88 s A-3A 233 I 3-CF ₃ 0 A-l

89 s A-3A 234 CF ₃ 3-CF ₃ 0 A-l

90 s A-3A 235 OMe 3-CF ₃ 0 A-l

91 s A-3A 236 Me 3-CF ₃ 0 A-l

92 s A-3A 237 F 4-Cl 0 A-l

93 s A-3A 238 CI 4-Cl 0 A-l

94 s A-3A 239 Br 4-Cl 0 A-l

95 s A-3A 240 I 4-Cl 0 A-l

96 s A-3A 241 CF ₃ 4-Cl 0 A-l

97 s A-3A 242 OMe 4-Cl 0 A-l

98 s A-3A 243 Me 4-Cl 0 A-l

99 0 A-3B 244 F 5-Cl 0 A-l

100 0 A-3B 245 CI 5-Cl 0 A-l

101 0 A-3B 246 Br 5-Cl 0 A-l

102 0 A-3B 247 I 5-Cl 0 A-l

103 0 A-3B 248 CF ₃ 5-Cl 0 A-l

104 0 A-3B 249 OMe 5-Cl 0 A-l

105 0 A-3B 250 Me 5-Cl 0 A-l

106 0 A-3B 251 F 6-Cl 0 A-l

107 0 A-3B 252 CI 6-Cl 0 A-l

108 0 A-3B 253 Br 6-Cl 0 A-l

109 0 A-3B 254 I 6-Cl 0 A-l

110 0 A-3B 255 CF ₃ 6-Cl 0 A-l

111 0 A-3B 256 OMe 6-Cl 0 A-l

112 0 A-3B 257 Me 6-Cl 0 A-l

113 0 A-3B 258 F 3 -Br, 4-F 0 A-l Header Row Header Row

Table A Table R2 (R ³ )m Z A

114 A-3B 259 CI 3 -Br, 4-F 0 A-l

115 A-3B 260 Br 3 -Br, 4-F 0 A-l

116 A-3B 261 I 3 -Br, 4-F 0 A-l

117 A-3B 262 CF ₃ 3 -Br, 4-F 0 A-l

118 A-3B 263 OMe 3 -Br, 4-F 0 A-l

119 A-3B 264 Me 3 -Br, 4-F 0 A-l

120 A-3B 265 F 3-F, 4-F 0 A-l

121 A-3B 266 CI 3-F, 4-F 0 A-l

122 A-3B 267 Br 3-F, 4-F 0 A-l

123 A-3B 268 I 3-F, 4-F 0 A-l

124 A-3B 269 CF ₃ 3-F, 4-F 0 A-l

125 A-3B 270 OMe 3-F, 4-F 0 A-l

126 A-3B 271 Me 3-F, 4-F 0 A-l

127 A-3B 272 F 3 -CI, 4-F 0 A-l

128 A-3B 273 CI 3 -CI, 4-F 0 A-l

129 A-3B 274 Br 3 -CI, 4-F 0 A-l

130 A-3B 275 I 3 -CI, 4-F 0 A-l

131 A-3B 276 CF ₃ 3 -CI, 4-F 0 A-l

132 A-3B 277 OMe 3 -CI, 4-F 0 A-l

133 A-3B 278 Me 3 -CI, 4-F 0 A-l

134 A-3B 279 F 3 -Br s A-l

135 A-3B 280 CI 3 -Br s A-l

136 A-3B 281 Br 3 -Br s A-l

137 A-3B 282 I 3 -Br s A-l

138 A-3B 283 CF ₃ 3 -Br s A-l

139 A-3B 284 OMe 3 -Br s A-l

140 A-3B 285 Me 3 -Br s A-l

141 A-3B 286 F 3 -CI s A-l

142 A-3B 287 CI 3 -CI s A-l

143 A-3B 288 Br 3 -CI s A-l

144 A-3B 289 I 3 -CI s A-l

145 A-3B 290 CF ₃ 3 -CI s A-l

146 A-3B 291 OMe 3 -CI s A-l

292 Me 3 -CI s A-l Table 293

The present disclosure also includes Tables 294 through 390. Each Table is constructed in the same manner as Table 293 above, except that the row heading in Table 293 (i.e. "R ² = F, (R ) _m = 3-F and Z = O") is replaced with the respective row heading shown below. For example, the header row in Table 294 is "R ² = CI, (R ) _m = 3-F and Z = O" and the first entry in Table 294 is a compound of Formula 1 wherein R ¹ = butylsulfinyl, R ² = CI, (R ) _m = 3-F and Z = O. Tables 295 through 390 are constructed similarly.

Header Row Header Row

Table R^ (R ³ )- Table R^ (R ³ )- Header Row Header Row

Header Row Header Row

A-4 A-5 A-6 A-7

R ² = F, (R ³ ) _m = 3-F and Z = O

A

A = A-4; R ⁴ = 3-bromopropyl A = A-5; R ⁵ = 4-chloro-3-butyn-l-yl

A = A-4; R ⁴ = tert-butyl) A = A-5; R^ = 3-chloro-2-propyn-l-yl A = A-4; R ⁴ = 3-chlorobutyl A = A-5; R ⁵ = 4,4-difluoro-2-butyn-l-yl A = A-4; R ⁴ = 3-chloropropyl A = A-5; R ⁵ = 5,5,5-trifluoro-l-methyl-2-pentyn-l-yl A = A-4; R ⁴ = 4,4-difluorobutyl A = A-5; R ⁵ = 5,5,5-trifluoro-2-pentyn-l-yl A = A-4; R ⁴ = 2,2-difluoroethyl A = A-5; R ⁵ = 5,5,5-trifluoro-3-pentyn-l-yl A A

A = A-4; R ⁴ = 3,3-difluoropropyl A = A-5; R ⁵ = 2-cyclobutylethyl

A = A-4; R ⁴ = ethyl A = A-5; R ⁵ = cyclohexyl

A = A-4; R ⁴ = hexyl A = A-5; R ⁵ = cyclopentylmethyl

A = A-4; R ⁴ = isobutyl A = A-5; R ⁵ = 2-cyclopropylethyl

A = A-4; R ⁴ = isopentyl A = A-5; R ⁵ = 3-cyclopropylpropyl

A = A-4; R ⁴ = metl yl A = A-5; R ⁵ = (2,2-dimethylcyclopropyl)methyl A = A-4; R ⁴ = 3,3,4,4,4-pentafluorobutyl A = A-5; R ⁵ = (l-methylcyclopropyl)methyl A = A-4; R ⁴ = 2,2,3,3,3-pentafluoropropyl A = A-5; R ⁵ = (2-methylcyclopentyl)methyl

A = A-4; R ⁴ = pentyl A = A-5; R ⁵ = (2-bromo-2-chloro-cyclopropyl)methyl A = A-4; R ⁴ = propyl A = A-5; R ⁵ = (2,2-dibromocyclopropyl)methyl A = A-4; R ⁴ = 3,3,4,4-tetrafluorobutyl A = A-5; R ⁵ = 2-(2,2-dichloro-l-methyl-cyclopropyl)etliyl A = A-4; R ⁴ = 2,2,3,3-tetrafluoropropyl A = A-5; R ⁵ = (2,2-dichloro-l-methyl-cyclopropyl)methyl A = A-4; R ⁴ = 3,3,3-trichloropropyl A = A-5; R ⁵ = 2-(3.3-difluorocyclobutyl)ethyl A = A-4; R ⁴ = 4,4,4-trifluorobutyl A = A-5; R ⁵ = 2-(2,2-difluorocyclopropyl)ethyl A = A-4; R ⁴ = 2,2,2-trifluoroethyl A = A-5; R ⁵ = (2,2-difluorocyclopropyl)methyl A = A-4; R ⁴ = 6,6,6-trifluorohexyl A = A-5; R ⁵ = 2-chloroethoxy methyl A = A-4; R ⁴ = 4.4.4-trifluoro-2-methyl-butyl A = A-5; R^ = 2,3-dicliloro-5-metho\y-pentyl A = A-4; R ⁴ = 3,3,3-trifluoropropyl A = A-5; R ⁵ = 3,3-difluoro-5-methoxy-pentyl A = A-4; R ⁴ = 3-bromopropyl A = A-5; R ⁵ = 2-isopropoxy ethyl

A = A-5; R ⁵ = butyl A = A-5; R ⁵ = 2-methoxyethyl A = A-5; R ⁵ = tert-butyl A = A-5; R^ = 5-methoxypentyl

A = A-5; R ⁵ = ethyl A = A-5; R ³ = 2-methoxypropyl A = A-5; R ⁵ = hexyl A = A-5; R ⁵ = 1,1,2.2-tetrafluoroetl oxymethyl A = A-5; R ⁵ = isobutyl A = A-5; R ⁵ = 2,2,2-trifluoroethox\'methyl A = A-5; R^ = isopentyl A = A-5; R ⁵ = 2-(trifluoromethoxy)ethyl A = A-5; R ⁵ = pentyl A = A-5; R ⁵ = 4-cyanobutyl

A = A-5; R ⁵ = propyl A = A-5; R ⁵ = 3-cyano-l,2-dimethyl-propyl A = A-5; R ⁵ = benzyl) A = A-5; R ³ = 2-cyanoethyl

A = A-5; R ⁵ = allyl A = A-5; R ⁵ = 3-cyano-2-methyl-propyl A = A-5; R ⁵ = 3-buten-l-yl A = A-5; R^ = cyanomethyl

A = A-5; R ³ = 3-methy-2-lbuten-l-yl A = A-5; R ³ = 5-cyanopentv'l

A = A-5; R ⁵ = 3-methyl-3-buten-l-yl A = A-5; R^ = 3-cyanopropyl

A = A-5; R^ = 4-methyl-3-penten-l-yl A = A-5; R ⁵ = 2-(cyanomethoxy)ethyl

A = A-5; R^ = 3-penten-l-yl A = A-5; R^ = 3-(cyanomethoxy)-2-methyl-propyl A = A-5; R ⁵ = 3-butyn-l-yl A = A-5; R^ = cyanomethox methyl A = A-5; R^ = 4-methyl-2-pentyn-l-yl A = A-5; R ⁵ = l,2-dimethyl-3-nitro-propyl

A = A-5; R ⁵ = 3-pentyn-l-yl A = A-5; R ³ = 4-hydroxybutyl A = A-5; R ³ = 2-propyn-l-yl A = A-5; R ³ = 3-hydroxy-l,2-dimethyl-propyl A = A-5; ^ = 5-hexyn-l-yl A = A-5; R ⁵ = 3-hydroxy-2-methyl-propyl A = A-5; R ⁵ = 4-pentyn-l-yl A = A-5; R ⁵ = hydroxymethyl

A = A-5; R^ = 3-bromopropyl A = A-5; R^ = 5-hydroxypentyl

A = A-5; R^ = 3-chlorobutyl A = A-5; R^ = 3 -hydroxy propyl

A = A-5; R^ = 3-chloropropyl A = A-5; R ⁵ = 2-methyl-3-nitro-propyl A = A-5; R ⁵ = 4,4-difluorobutyl A = A-5; R ⁵ = 4-nitrobutyl

A = A-5; R ⁵ = 2,2-difluoroethyl A = A-5; R ⁵ = 2-nitroethyl

A = A-5; R ³ = 3,3-difluoropropyl A = A-5; R ³ = nitromethyl

A = A-5; R ⁵ = 3,3,4,4,4-pentafluorobutyl A = A-5; R ⁵ = 5-nitropentyl

A = A-5; R ⁵ = 2,2,3,3,3-pentafluoropropyl A = A-5; R ⁵ = 3-nitropropyl

A = A-5; R ³ = 3,3,4,4-tetrafluorobutyl A = A-5; R^ = 2-cliloroethylthio methyl A = A-5; R ⁵ = 2,2,3,3-tetrafluoropropyl A = A-5; R ⁵ = 2,3-dichloro-5-metliylthio-pentyl A = A-5; R ⁵ = 3,3,3-trichloropropyl A = A-5; R ⁵ = 3,3-difluoro-5-methylthio-pentyl A = A-5; R ⁵ = 4,4,4-trifluorobutyl A = A-5; R ⁵ = 2-isopropylthioethyl A = A-5; R ⁵ = 2,2,2-trifluoroethyl A = A-5; R ⁵ = 2-methylthioethyl

A = A-5; R^ = 6,6,6-trifluorohexyl A = A-5; R ⁵ = 5-methylthiopentyl

A = A-5; R ⁵ = 4,4,4-trifluoro-2-methyl-bu1yl A = A-5; R ⁵ = 2-methylthiopropyl

A = A-5; R ³ = 3,3,3-trifluoropropyl A = A-5; R ⁵ = 1,1,2,2-tetrafluoroethyltliiomethyl A = A-5; R^ = 4-bromo-3-buten-l-yl A = A-5; R ⁵ = 2,2,2-trifluoroetliylthiomethyl A = A-5; R ⁵ = 2-chloroallyl A = A-5; R ⁵ = 2-(trifluoromethylthio)ethyl A = A-5; R ⁵ = 3-chloroallyl A = A-6; R ^6a = Me); R ^6b = butyl

A = A-5; R^ = 3-chloro-3-buten-l-yl A = A-6; R ^6a = Me; R ^6b = tert-butyl A = A-5; R ⁵ = 4-chloro-3-buten-l-yl A = A-6; R ^6a = Me; R ^6b = ethyl

A = A-5; R^ = 5,5-difluoro-3-penten-l-yl A = A-6; R ^6a = Me; R ^6b = Isobutyl A = A-5; R ⁵ = 4,4,4-trifluoro-2-buten-l-yl A = A-6; R ^6a = Me; R ^6b = propyl A = A-5; R ⁵ = 5,5,5-trifluoro-3-methyl-2- penten-l-yl A = A-6; R ^6a = ethylX ; R ^6b = ethyl A = A-5; R^ = 5.5.5-trifluoro-3-penten-l-yl A = A-6; R ^6a = Me; R ^6b = 3,3,3-trifluoropropyl A = A-5; R^ = 4-bromo-3-butyn-l-yl A = A-6; R ^6a = Me; R ^6b = 2,2,3,3,3-pentafluoropropyl

A = A-6; R ^6a = 3,3,3-trifluoropropyl; R ^6b = 3,3,3-

A = A-5; R ⁵ = 3-butyn-l-yl trifluoropropyl

A = A-7; R^ = isopentyl A = A-7; R ¹⁵ = ethyl

A = A-7; R ¹⁵ = pentyl A = A-7; R ¹⁵ = hexyl

A = A-7; R ¹⁵ = propyl A = A-7; R ¹⁵ = isobutyl

A = A-7; R ¹⁵ = H A = A-7; R ¹⁵ = methyl The present disclosure also includes Tables 392 through 585. Each Table is constructed in the same manner as Table 391 above, except that the row heading in Table 391 (i.e. "R ² = F, (R ) _m = 3-F and Z = O") is replaced with the respective row heading shown below. For example, the header row in Table 392 is "R ² = CI, (R ) _m = 3-F and Z = O" and the first entry in Table 392 is a compound of Formula 1 wherein R ¹ = 3-bromopropyl, R ² = CI, (R ) _m = 3-F and Z = O. Tables 392 through 585 are constructed similarly.

Header Row Header Row

Header Row Header Row

Header Row Header Row

The present disclosure also includes Tables 586 through 684. Each Table is constructed in the same manner as Table 1 above, except that the row heading in Table 1 (i.e. "R ² = F, (R ³ ) _m = 3-F, Z = O and A = A-4") is replaced with the respective row heading shown below. For example, the first entry in Table 586 is a compound of Formula 1 wherein R ² is CI, (R ³ ) _m is 3-F, Z is O, A is A-3A and R ¹ is butyl. Tables 587 through 684 are constructed similarly.

Header Row

Table A

586 A-2

587 A-2

588 A-2

589 A-2

590 A-2

591 A-2

592 A-2

593 A-2

594 A-2

595 A-2

596 A-2

597 A-2

598 A-2

599 A-2

600 A-2

601 A-2

602 A-2

603 A-2

604 A-2

605 A-2

606 A-2

607 A-2

608 A-2

609 A-2

610 A-2

611 A-2

612 A-2

613 A-2

614 A-2

615 A-2

616 A-2

617 A-2

618 A-2

619 A-2 A

A-2

A-2

A-2

A-2

A-2

A-2

A-2

A-2

A-2

A-2

A-2

A-2

A-2

A-2

A-2

A compound of this invention will generally be used as a herbicidal active ingredient in a composition, i.e. formulation, with at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents, which serves as a carrier. The formulation or composition ingredients are selected to be consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature.

Useful formulations include both liquid and solid compositions. Liquid compositions include solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions, oil-in -water emulsions, flowable concentrates and/or suspoemulsions) and the like, which optionally can be thickened into gels. The general types of aqueous liquid compositions are soluble concentrate, suspension concentrate, capsule suspension, concentrated emulsion, microemulsion, oil-in-water emulsion, flowable concentrate and suspo-emulsion. The general types of nonaqueous liquid compositions are emulsifiable concentrate, microemulsifiable concentrate, dispersible concentrate and oil dispersion.

The general types of solid compositions are dusts, powders, granules, pellets, prills, pastilles, tablets, filled films (including seed coatings) and the like, which can be water-dispersible ("wettable") or water-soluble. Films and coatings formed from film- forming solutions or flowable suspensions are particularly useful for seed treatment. Active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively the entire formulation of active ingredient can be encapsulated (or "overcoated"). Encapsulation can control or delay 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 primarily used as intermediates for further formulation.

Sprayable formulations are typically extended in a suitable medium before spraying. Such liquid and solid formulations are formulated to be readily diluted in the spray medium, usually water, but occasionally another suitable medium like an aromatic or paraffinic hydrocarbon or vegetable oil. Spray volumes can range from about from about one to several thousand liters per hectare, but more typically are in the range from about ten to several hundred liters per hectare. Sprayable formulations can be tank mixed with water or another 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 metered directly into drip irrigation systems or metered into the furrow during planting.

The formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up to 100 percent by weight.

Weight Percent

Active

Ingredient Diluent Surfactant

Water-Dispersible and Water-soluble 0.001-90 0-99.999 0-15

Granules, Tablets and Powders

Oil Dispersions, Suspensions, 1-50 40-99 0-50

Emulsions, Solutions (including

Emulsifiable Concentrates)

Dusts 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 (e.g., 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, N,N-dimethylalkanamides (e.g., N,N-dimethylformamide), limonene, dimethyl sulfoxide, N-alkylpyrrolidones (e.g., N-methylpyrrolidinone), alkyl phosphates (e.g., tri ethyl phosphate), ethylene glycol, Methylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, propylene carbonate, butylene carbonate, paraffins (e.g., white mineral oils, normal paraffins, isoparaffins), alkylbenzenes, alkylnaphthalenes, glycerine, 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 can be linear, branched, saturated or unsaturated, such as methanol, ethanol, «-propanol, isopropyl alcohol, «-butanol, isobutyl alcohol, «-hexanol, 2-ethylhexanol, «-octanol, decanol, isodecyl alcohol, 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 C6-C22), such as plant seed and fruit oils (e.g., oils of olive, castor, linseed, sesame, corn (maize), peanut, sunflower, grapeseed, safflower, cottonseed, soybean, rapeseed, coconut and palm kernel), animal-sourced fats (e.g., beef tallow, pork tallow, lard, cod liver oil, fish oil), and mixtures thereof. Liquid diluents also include alkylated fatty acids (e.g., methylated, ethylated, butylated) wherein the fatty acids may 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 invention often include one or more surfactants. When added to a liquid, surfactants (also known as "surface-active agents") generally modify, most often reduce, the surface tension of the liquid. Depending on the nature of the hydrophilic and lipophilic groups in a surfactant molecule, surfactants can be useful as wetting agents, dispersants, emulsifiers or defoaming agents.

Surfactants can be classified as nonionic, anionic or cationic. Nonionic surfactants useful 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 prepared from the alcohols and ethylene oxide, propylene oxide, 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 prepared from ethylene oxide or propylene oxide and reverse block polymers where the terminal blocks are prepared 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 peg (polyethylene glycol) resins, graft or comb polymers and star polymers; polyethylene glycols (pegs); 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 lignin derivatives such as lignosulfonates; maleic or succinic acids or their anhydrides; olefin sulfonates; phosphate esters such as phosphate esters of alcohol alkoxylates, phosphate esters of alkylphenol alkoxylates and phosphate esters of styryl phenol ethoxylates; protein-based surfactants; sarcosine derivatives; styryl phenol ether sulfate; sulfates and sulfonates of oils and fatty acids; sulfates and sulfonates of ethoxylated alkylphenols; sulfates of alcohols; sulfates of ethoxylated alcohols; sulfonates of amines and amides such as N,N-alkyltaurates; sulfonates of benzene, cumene, toluene, xylene, and dodecyl and tridecylbenzenes; sulfonates of condensed naphthalenes; sulfonates of naphthalene and alkyl naphthalene; sulfonates of fractionated petroleum; 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 N-alkyl propanediamines, tripropylenetriamines 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 disclosed 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.

Compositions of this invention 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 may control: pH (buffers), foaming during processing (antifoams such polyorganosiloxanes), sedimentation of active ingredients (suspending agents), viscosity (thixotropic thickeners), in-container microbial growth (antimicrobials), product freezing (antifreezes), color (dyes/pigment dispersions), wash-off (film formers or stickers), 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, annual International and North American editions published by McCutcheon' s Division, The Manufacturing Confectioner Publishing Co.; and PCT Publication WO 03/024222.

The compound of Formula 1 and any other active ingredients are typically incorporated 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 water-immiscible, an emulsifier is typically added to emulsify the active-containing solvent upon dilution with water. Active ingredient slurries, with particle diameters of up to 2,000 μπι can be wet milled using media mills to obtain particles with average diameters below 3 μπι. 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 usually require dry milling processes, which produce average particle diameters in the 2 to 10 μπι range. Dusts and powders can be prepared by blending and usually grinding (such as with a hammer mill or fluid-energy mill). Granules and pellets can be prepared by spraying the active material upon 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 and following, and WO 91/13546. Pellets can be prepared as described in U.S. 4,172,714. Water-dispersible and water-soluble granules can be prepared as taught in U.S. 4,144,050, U.S. 3,920,442 and DE 3,246,493. Tablets can be prepared as taught in 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 further information regarding the art of formulation, see T. S. Woods, "The Formulator's Toolbox - Product Forms for Modern Agriculture" in Pesticide Chemistry and Bioscience, 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 through 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 conventional ways. Compound numbers refer to compounds in Index Table A. Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. The following Examples are, therefore, to be construed as merely illustrative, and not limiting of the disclosure in any way whatsoever. Percentages are by weight except where otherwise indicated.

Example A

High Strength Concentrate

Compound 1 98.5% silica aerogel 0.5% synthetic amorphous fine silica 1.0%

Example B

Wettable Powder

Compound 1 65.0% dodecylphenol polyethylene glycol ether 2.0% sodium ligninsulfonate 4.0%> sodium silicoaluminate 6.0% montmorillonite (calcined) 23.0%

Example C

Granule

Compound 1 10.0% attapulgite granules (low volatile matter, 0.71/0.30 mm; 90.0% U.S.S. No. 25-50 sieves)

Example D

Extruded Pellet

Compound 1 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate 5.0%> sodium alkylnaphthalenesulfonate 1.0% calcium/magnesium bentonite 59.0%>

Example E

Emulsifiable Concentrate

Compound 1 10.0% polyoxyethylene sorbitol hexoleate 20.0%

Cg-Cio fatty acid methyl ester 70.0%

Example F

Microemulsion

Compound 1 5.0% polyvinylpyrrolidone-vinyl acetate copolymer 30.0% alkylpolyglycoside 30.0% glyceryl monooleate 15.0% water 20.0%

Example G

Suspension Concentrate

Compound 1 35% butyl polyoxyethylene/polypropylene 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 based defoamer 0.1% l,2-benzisothiazolin-3-one 0.1% water 53.7%

Example H

Emulsion in Water

Compound 1 10.0% butyl polyoxyethylene/polypropylene 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 based defoamer 0.1% l,2-benzisothiazolin-3-one 0.1% aromatic petroleum based hydrocarbon 20.0 water 58.7%

Example I

Oil Dispersion

Compound 1 25% polyoxyethylene sorbitol hexaoleate 15% organically modified bentonite clay 2.5% fatty acid methyl ester 57.5% The present disclosure also includes Examples A through I above except

"Compound 1" is replaced with "Compound 2", "Compound 3", "Compound 4

"Compound 5", "Compound 6", "Compound 7", "Compound 8", "Compound 9

"Compound 10", "Compound 11", "Compound 12", "Compound 13", "Compound 14

"Compound 15", "Compound 16", "Compound 17", "Compound 18", "Compound 19

"Compound 20", "Compound 21", "Compound 22", "Compound 23", "Compound 24

"Compound 25", "Compound 26", "Compound 27", "Compound 28", "Compound 29

"Compound 30", "Compound 31", "Compound 32", "Compound 33", "Compound 34

"Compound 35", "Compound 36", "Compound 37", "Compound 38", "Compound 39

"Compound 40", "Compound 41", "Compound 42", "Compound 43", "Compound 44

"Compound 45", "Compound 46", "Compound 47", "Compound 48", "Compound 49

"Compound 50", "Compound 51", "Compound 52", "Compound 53", "Compound 54

"Compound 55", "Compound 56", "Compound 57", "Compound 58", "Compound 59

"Compound 60", "Compound 61", "Compound 62", "Compound 63", "Compound 64

"Compound 65", "Compound 66", "Compound 67", "Compound 68", "Compound 69

"Compound 70", "Compound 71", "Compound 72", "Compound 73", "Compound 74

"Compound 75", "Compound 76", "Compound 77", "Compound 78", "Compound 79

"Compound 80", "Compound 81", "Compound 82", "Compound 83", "Compound 84

"Compound 85", "Compound 86", "Compound 87", "Compound 88", "Compound 89

"Compound 90", "Compound 91", "Compound 92", "Compound 93", "Compound 94

"Compound 95", "Compound 96", "Compound 97", "Compound 98", "Compound 99

"Compound 100", "Compound 101", "Compound 102", "Compound 103", "Compound 104", "Compound 104", "Compound 106", "Compound 107", "Compound 108", "Compound 109", "Compound 110", "Compound 111", "Compound 112", "Compound 113", "Compound 114", "Compound 115", "Compound 116", "Compound 117", "Compound 118", "Compound 119", "Compound 120", "Compound 121", "Compound 122", "Compound 123", "Compound 124", "Compound 125", "Compound 126", "Compound 127", "Compound 128", "Compound 129", "Compound 130", "Compound 131", "Compound 132", "Compound 133", "Compound 134", "Compound 135", "Compound 136", "Compound 137", "Compound 138", "Compound 139", "Compound 140", "Compound 141", "Compound 142", "Compound 143", "Compound 144", "Compound 145" or "Compound 146".

Test results indicate that the compounds of the present invention are highly active preemergent and/or postemergent herbicides and/or plant growth regulants. The compounds of the inention generally show highest activity for postemergence weed control (i.e. applied after weed seedlings emerge from the soil) and preemergence weed control (i.e. applied before weed seedlings emerge from the soil). Many of them have utility for broad-spectrum pre- and/or postemergence weed control in areas where complete control of all vegetation is desired such as around fuel storage tanks, industrial storage areas, parking lots, drive-in theaters, air fields, river banks, irrigation and other waterways, around billboards and highway and railroad structures. Many of the compounds of this invention, by virtue of selective metabolism in crops versus weeds, or by selective activity at the locus of physiological inhibition in crops and weeds, or by selective placement on or within the environment of a mixture of crops and weeds, 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 selectivity factors within a compound or group of compounds can readily be determined by performing routine biological and/or biochemical assays. Compounds of this invention may show tolerance to important agronomic crops including, but is not limited to, alfalfa, barley, cotton, wheat, rape, sugar beets, corn (maize), sorghum, soybeans, rice, oats, peanuts, vegetables, tomato, potato, perennial plantation crops including coffee, cocoa, oil palm, rubber, sugarcane, citrus, grapes, fruit trees, nut trees, banana, plantain, pineapple, hops, tea and forests such as eucalyptus and conifers (e.g., loblolly pine), and turf species (e.g., Kentucky bluegrass, St. Augustine grass, Kentucky fescue and Bermuda grass). Compounds of this invention can be used in 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 to modify plant growth.

As the compounds of the invention have both preemergent and postemergent herbicidal activity, to control undesired vegetation by killing or injuring the vegetation or reducing its growth, the compounds can be usefully applied by a variety of methods involving contacting a herbicidally effective amount of a compound of the invention, or a composition comprising said compound and at least one of a surfactant, a solid diluent or a liquid diluent, to the foliage or other part of the undesired vegetation or to the environment of the undesired vegetation such as the soil or water in which the undesired vegetation is growing or which surrounds the seed or other propagule of the undesired vegetation.

A herbicidally effective amount of the compounds of this invention 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 invention 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 easily determine the herbicidally effective amount necessary for the desired level of weed control.

In one common embodiment, a compound of the invention is applied, typically in a formulated composition, to a locus comprising desired vegetation (e.g., crops) and undesired vegetation (i.e. weeds), both of which may be seeds, seedlings and/or larger plants, in contact with a growth medium (e.g., soil). In this locus, a composition comprising a compound of the invention can be directly applied to a plant or a part thereof, particularly of the undesired vegetation, and/or to the growth medium in contact with the plant.

Plant varieties and cultivars of the desired vegetation in the locus treated with a compound of the invention can 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's genome. A transgene that is defined by its particular location in the plant genome is called a transformation or transgenic event.

Genetically modified plant cultivars in the locus which can be treated according to the invention include those that are resistant against one or more biotic stresses (pests such as nematodes, insects, mites, fungi, etc.) or abiotic stresses (drought, cold temperature, soil salinity, etc.), or that contain other desirable characteristics. Plants can be genetically modified to exhibit traits of, for example, herbicide tolerance, insect-resistance, modified oil profiles or drought tolerance. Useful genetically modified plants containing single gene transformation events or combinations of transformation events are listed in Exhibit C. Additional information for the genetic modifications listed in Exhibit C can be obtained from publicly available databases maintained, for example, by the U.S. Department of Agriculture.

The following abbreviations, Tl through T37, are used in Exhibit C for traits. A "-" means the entry is not avail ble "tol." means "tolerance" and " s." means resistance.

Trait Description Trait Description

Tl Glyphosate tol. T27 High tryptophan

T2 High lauric acid oil T28 Erect leaves semidwarf

T3 Glufosinate tol. T29 Semidwarf

T4 Phytate breakdown T30 Low iron tol.

T5 Oxynil tol. T31 Modified oil/fatty acid

T6 Disease res. T32 HPPD tol.

T7 Insect res. T33 High oil

T9 Modified flower color T34 Aryloxyalkanoate tol.

Ti l ALS Herbicide tol. T35 Mesotrione tol.

T12 Dicamba tol. T36 Reduced nicotine

T13 Anti-allergy T37 Modified product

T14 Salt tol.

Exhibit C

Crop Event Name Event Code Trait(s) Gene(s)

Alfalfa J101 MON-00101-8 Tl cp4 epsps (aroA:CP4)

MON-00163-

Alfalfa J163 Tl cp4 epsps (aroA:CP4)

7

Canola* 23-18-17 (Event 18) CGN-89465-2 T2 te Crop Event Name Event Code Trait(s) Gene(s)

Canola* 23-198 (Event 23) CGN-89465-2 T2 te

Canola* 61061 DP-061061-7 Tl gat4621

Canola* 73496 DP-073496-4 Tl gat4621

Canola* GT200 (RT200) MON-89249-2 Tl cp4 epsps (aroA:CP4); goxv247

Canola* MON-00073-

GT73 (RT73) Tl

7 cp4 epsps (aroA:CP4); goxv247

Canola* HCN10 (Topas 19/2) - T3 bar

ACS-BN008-

Canola* HCN28 (T45) T3 pat (syn)

2

ACS-BN007-

Canola* HCN92 (Topas 19/2) T3 bar

1

MON-88302-

Canola* MON88302 Tl

9 cp4 epsps (aroA:CP4)

Canola* MPS961 - T4 phyA

Canola* MPS962 - T4 phyA

Canola* MPS963 - T4 phyA

Canola* MPS964 - T4 phyA

Canola* MPS965 - T4 phyA

ACS-BN004-

Canola* MSI (B91-4) T3 bar

7

ACS-BN005-

Canola* MS8 T3

8 bar

ACS-BN011-

Canola* OXY-235 T5 bxn

5

Canola* PHY 14 - T3 bar

Canola* PHY23 - T3 bar

Canola* PHY35 - T3 bar

Canola* PHY36 - T3 bar

ACS-BN001-

Canola* RF1 (B93-101) T3 bar

4

ACS-BN002-

Canola* RF2 (B94-2) T3 bar

5

ACS-BN003-

Canola* RF3 T3 bar

6

Bean EMBRAPA 5.1 EMB-PV051-1 T6 acl (sense and antisense)

Brinjal # EE-1 - T7 cry 1 Ac

Cotton 19-51a DD-01951A-7 Til S4-HrA

Cotton 281-24-236 DAS-24236-5 T3.T7 pat (syn); cry IF

Cotton 3006-210-23 DAS-21023-5 T3,T7 pat (syn); cry 1 Ac

Cotton 31707 - T5,T7 bxn; cry 1 Ac

Cotton 31803 - T5,T7 bxn; cry 1 Ac

Cotton 31807 - T5,T7 bxn; cry 1 Ac

Cotton 31808 - T5,T7 bxn; cry 1 Ac

Cotton 42317 - T5,T7 bxn; crvTAc

Cotton BNLA-601 - T7 cry 1 Ac

Cotton BXN10211 BXN10211-9 T5 bxn; cry 1 Ac Crop Event Name Event Code Trait(s) Gene(s)

Cotton BXN10215 BXN10215-4 T5 bxn; cry 1 Ac

Cotton BXN10222 BXN10222-2 T5 bxn; cry 1 Ac

Cotton BXN10224 BXN10224-4 T5 bxn; crylAc

Cotton COT102 SYN-IR102-7 T7 vip3A(a)

Cotton COT67B SYN-IR67B-1 T7 crylAb

Cotton COT202 - T7 vip3A

Cotton Event 1 - T7 cry 1 Ac

GTL-

Cotton GMF CrylA T7

GMF311-7 crylAb-Ac

Cotton GHB119 BCS-GH005-8 T7 cry2Ae

Cotton GHB614 BCS-GH002-5 Tl 2mepsps

Cotton GK12 - T7 crylAb- Ac

Cotton LLCotton25 ACS-GHOOl-3 T3 bar

Cotton MLS 9124 - T7 crylC

Cotton MON1076 MON-89924-2 T7 cry 1 Ac

Cotton MON1445 MON-01445-2 Tl cp4 epsps (aroA:CP4)

Cotton MON15985 MON-15985-7 T7 crylAc; cry2Ab2

Cotton MON1698 MON-89383-1 T7 cp4 epsps (aroA:CP4)

Cotton MON531 MON-00531-6 T7 crylAc

Cotton MON757 MON-00757-7 T7 crylAc

Cotton MON88913 MON-88913-8 Tl cp4 epsps (aroA:CP4)

Cotton Nqwe Chi 6 Bt - T7 -

Cotton SKG321 - T7 crylA; CpTI

Cotton T303-3 BCS-GH003-6 T3,T7 crylAb; bar

Cotton T304-40 BCS-GH004-7 T3,T7 crylAb; bar

Cotton CE43-67B - T7 crylAb

Cotton CE46-02A - T7 crylAb

Cotton CE44-69D - T7 crylAb

Cotton 1143-14A - T7 crylAb

Cotton 1143-51B - T7 crylAb

Cotton T342-142 - T7 crylAb

Cotton PV-GHGT07 (1445) - Tl cp4 epsps (aroA:CP4)

Cotton EE-GH3 - Tl mepsps

Cotton EE-GH5 - T7 crylAb

Cotton MON88701 MON-88701-3 T3,T12 Modified dmo; bar

Cotton OsCrl l - T13 Modified Cry j

Flax FP967 CDC-FLOOl-2 Ti l als

Lentil RH44 - T16 als

Maize 3272 SYN-E3272-5 T17 amy797E

Maize 5307 SYN-05307-1 T7 ecryS.lAb

Maize 59122 DAS-59122-7 Τ3/Γ7 cry34Abl; cry35Abl; pat Crop Event Name Event Code Trait(s) Gene(s)

Maize 676 PH-000676-7 Τ3/Π8 pat; dam

Maize 678 PH-000678-9 T3,T18 pat; dam

Maize 680 PH-000680-2 T3,T18 pat; dam

Maize 98140 DP-098140-6 Tl/Tl l gat4621; zm-hra

Maize BtlO - T3,T7 crylAb; pat

Maize Btl76 (176) SYN-EV176-9 T3,T7 cr lAb; bar

Maize BVLA430101 - T4 phyA2

Maize CBH-351 ACS-ZM004-3 T3,T7 cry9C; bar

Maize DAS40278-9 DAS40278-9 T19 aad-1

Maize DBT418 DKB-89614-9 T3,T7 cry 1 Ac; pinll; bar

Maize DLL25 (B16) D B-89790-5 T3 bar

Maize GA21 MON-00021-9 Tl mepsps

Maize GG25 - Tl mepsps

Maize GJ11 - Tl mepsps

Maize F1117 - Tl mepsps

Maize GAT-ZM1 - T3 pat

Maize LY038 REN-00038-3 T20 cordapA

Maize MIR162 SY -IR162-4 T7 vip3Aa20

Maize MIR604 SYN-IR604-5 T7 mcr 3A

Maize MON801 (MON80100) MON801 crylAb; cp4 epsps (aroA:CP4);

T1,T7

goxv247

Maize MON802 MON-80200-7 crylAb; cp4 epsps (aroA:CP4);

T1,T7

goxv247

PH-MON-809-

Maize MON809 crylAb; cp4 epsps (aroA:CP4);

T1,T7

2 goxv247

Maize MON810 MON-00810-6 crylAb; cp4 epsps (aroA:CP4);

T1,T7

goxv247

Maize MON832 - Tl cp4 epsps (aroA:CP4); goxv247

Maize MON863 MON-00863-5 T7 cry3Bbl

Maize MON87427 MON-87427-7 Tl cp4 epsps (aroA:CP4)

Maize MON87460 MON-87460-4 T21 cspB

Maize MON88017 MON-88017-3 T1,T7 cry3Bbl; cp4 epsps (aroA:CP4)

Maize MON89034 MON-89034-3 T7 cry2Ab2; cry 1 A.105

Maize MS3 ACS-ZMOOl-9 T3,T18 bar; barnase

Maize MS6 ACS-ZM005-4 T3,T18 bar; barnase

Maize NK603 MON-00603-6 Tl cp4 epsps (aroA:CP4)

Maize T14 ACS-ZM002-1 T3 pat (syn)

Maize T25 ACS-ZM003-2 T3 pat (syn)

Maize TCI 507 DAS-01507-1 T3,T7 crylFa2; pat

Maize TC6275 DAS-06275-8 T3,T7 mocrylF; bar

Maize VIP 1034 - T3,T7 vip3A; pat

Maize 43A47 DP-043A47-3 T3,T7 cry IF; cry34Abl; cry35Abl; pat

Maize 40416 DP-040416-8 T3,T7 cry IF; cry34Abl; cry35Abl; pat Crop

Rice

Rice

Rice

Rice

Rice

Rice

Rice

Rice

Rice

Rice

Rice

Rose

Rose

Soybean

Soybean

Soybean

Soybean

Soybean

Soybean

Soybean

Soybean

Soybean

Soybean

Soybean

Soybean

Soybean

Soybean

Soybean

Soybean

Soybean

Soybean

Soybean

Soybean

Soybean

Soybean Crop Event Name Gene(s)

Soybean SYHT04R Modified avhppd

Soybean 9582.814.19.1 cry 1 Ac, cry IF, PAT

Squash CZW3 cmv cp, zymv cp, wmv cp

Squash ZW20 zymv cp, wmv cp

Sugar Beet GTSB77 (T9100152) cp4 epsps (aroA:CP4); goxv247

Sugar Beet H7-1 cp4 epsps (aroA:CP4)

Sugar Beet T120-7 pat

Sugar Beet T227-1 cp4 epsps (aroA:CP4)

Sugarcane NXI-1T EcbetA

Sunflower X81359 als

Pepper PK-SP01 cmv cp

Tobacco C/F/93/08-02 bxn

Tobacco Vector 21-41 NtQPTl (antisense)

Sunflower X81359 als

Wheat MON71800 cp4 epsps (aroA:CP4)

* Argentine (Brassica napus), ** Polish (B. rapa), # Eggplant

Although most typically, compounds of the invention are used to control undesired vegetation, contact of desired vegetation in the treated locus with compounds of the invention may result in super-additive or synergistic effects with genetic traits in the desired vegetation, including 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 greater than expected from the genetic traits in the desired vegetation.

An embodiment of the present invention is a method for controlling the growth of undesired vegetation in genetically modified plants that exhibit traits of glyphosate tolerance, glufosinate tolerance, ALS herbicide tolerance, dicamba tolerance, imidazolinone herbicide tolerance, 2,4-D tolerance, HPPD tolerance and mesotrione tolerance, comprising contacting the vegetation or its environment with a herbicidally effective amount of a compound of Formula 1.

Compounds of this invention can also be mixed with one or more other biologically active compounds or agents including herbicides, herbicide safeners, fungicides, insecticides, nematocides, bactericides, acaricides, growth regulators such as insect molting inhibitors and rooting stimulants, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants, plant nutrients, other biologically active compounds or entomopathogenic bacteria, virus or fungi to form a multi-component pesticide giving an even broader spectrum of agricultural protection. Mixtures of the compounds of the invention with other herbicides can broaden the spectrum of activity against additional weed species, and suppress the proliferation of any resistant biotypes. Thus the present invention also pertains to a composition comprising a compound of Formula 1 (in a herbicidally effective amount) and at least one additional biologically active compound or agent (in a biologically effective amount) and can further comprise at least one of a surfactant, a solid diluent or a liquid diluent. The other biologically active compounds or agents can be formulated in compositions comprising at least one of a surfactant, solid or liquid diluent. For mixtures of the present invention, one or more other biologically active compounds or agents can be formulated together with a compound of Formula 1, to form a premix, or one or more other biologically active compounds or agents can be formulated separately from the compound of Formula 1, and the formulations combined together before application (e.g., in a spray tank) or, alternatively, applied in succession.

A mixture of one or more of the following herbicides with a compound of this invention may be particularly useful for weed control: acetochlor, acifluorfen and its sodium salt, aclonifen, acrolein (2-propenal), alachlor, alloxydim, ametryn, amicarbazone, amidosulfuron, aminocyclopyrachlor and its esters (e.g., methyl, ethyl) and salts (e.g., sodium, potassium), aminopyralid, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, bencarbazone, benfluralin, benfuresate, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyrone, bifenox, bilanafos, bispyribac and its sodium salt, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil octanoate, butachlor, butafenacil, butamifos, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone-ethyl, catechin, chlomethoxyfen, chloramben, chlorbromuron, chlorflurenol-methyl, chloridazon, chlorimuron-ethyl, chlorotoluron, chlorpropham, chl or sulfur on, chlorthal-dimethyl, chlorthiamid, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clefoxydim, clethodim, clodinafop-propargyl, clomazone, clomeprop, clopyralid, clopyralid-olamine, cloransulam- methyl, cumyluron, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop-butyl, 2,4-D and its butotyl, butyl, isoctyl and isopropyl esters and its dimethylammonium, diolamine and trolamine salts, daimuron, dalapon, dalapon-sodium, dazomet, 2,4-DB and its dimethylammonium, potassium and sodium salts, desmedipham, desmetryn, dicamba and its diglycolammonium, dimethylammonium, potassium and sodium salts, dichlobenil, dichlorprop, diclofop-methyl, diclosulam, difenzoquat metilsulfate, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimethipin, dimethylarsinic acid and its sodium salt, dinitramine, dinoterb, diphenamid, diquat dibromide, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanid, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, fenuron, fenuron-TCA, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop-butyl, fluazifop-P -butyl, fluazolate, flucarbazone, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac-pentyl, flumioxazin, fluometuron, fluoroglycofen-ethyl, flupoxam, flupyrsulfuron-methyl and its sodium salt, flurenol, flurenol -butyl, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet-methyl, fomesafen, foramsulfuron, fosamine-ammonium, glufosinate, glufosinate-ammonium, glufosinate-P, glyphosate and its salts such as ammonium, isopropylammonium, potassium, sodium (including sesquisodium) and trimesium (alternatively named sulfosate), halauxifen, halauxifen-methyl, halosulfuron-methyl, haloxyfop-etotyl, haloxyfop-methyl, hexazinone, hydantocidin, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-ammonium, imazosulfuron, indanofan, indaziflam, iofensulfuron, iodosulfuron-methyl, ioxynil, ioxynil octanoate, ioxynil-sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, isoxachlortole, lactofen, lenacil, linuron, maleic hydrazide, MCPA and its salts (e.g., MCPA-dimethylammonium, MCPA- potassium and MCPA-sodium, esters (e.g., MCPA-2-ethylhexyl, MCPA-butotyl) and thioesters (e.g., MCPA-thioethyl), MCPB and its salts (e.g., MCPB-sodium) and esters (e.g., MCPB -ethyl), mecoprop, mecoprop-P, mefenacet, mefluidide, mesosulfuron-methyl, mesotrione, metam-sodium, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methylarsonic acid and its calcium, monoammonium, monosodium and disodium salts, methyldymron, metobenzuron, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron-methyl, molinate, monolinuron, naproanilide, napropamide, napropamide-M, naptalam, neburon, nicosulfuron, norflurazon, orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat dichloride, pebulate, pelargonic acid, pendimethalin, penoxsulam, pentanochlor, pentoxazone, perfluidone, pethoxamid, pethoxyamid, phenmedipham, picloram, picloram-potassium, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen-ethyl, pyrasulfotole, pyrazogyl, pyrazolynate, pyrazoxyfen, pyrazosulfuron-ethyl, pyribenzoxim, pyributicarb, pyridate, pyriftalid, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron-methyl, sulfosulfuron, 2,3,6- TBA, TCA, TCA-sodium, tebutam, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbumeton, terbuthylazine, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thifensulfuron-methyl, thiobencarb, tiafenacil, tiocarbazil, tolpyralate, topramezone, tralkoxydim, tri-allate, triafamone, triasulfuron, triaziflam, tribenuron-methyl, triclopyr, triclopyr-butotyl, triclopyr-triethylammonium, tridiphane, trietazine, trifloxysulfuron, trifludimoxazin, trifluralin, triflusulfuron-methyl, tritosulfuron, vernolate, 3-(2-chloro-3,6- difluorophenyl)-4-hy droxy- 1 -methyl- 1 , 5 -naphthyridin-2( lH)-one, 5 -chloro-3 - [(2-hy droxy-6- oxo- 1 -cyclohexen- 1 -yl)carbonyl]- 1 -(4-methoxyphenyl)-2( lH)-quinoxalinone, 2-chloro-N- (1 -methyl- lH-tetrazol-5-yl)-6-(trifluoromethyl)-3-pyridinecarboxamide, 7-(3,5-dichloro-4- pyridinyl)-5-(2,2-difluoroethyl)-8-hydroxypyrido[2,3-^]pyraz in-6(5H)-one), 4-(2,6-diethyl- 4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone), 5-[[(2,6- difluorophenyl)methoxy]methyl]-4,5-dihydro-5-methyl-3-(3-met hyl-2-thienyl)isoxazole (previously methioxolin), 4-(4-fluorophenyl)-6-[(2-hydroxy-6-oxo- 1 -cyclohexen- 1 - yl)carbonyl]-2-methyl-l,2,4-triazine-3,5(2H,4H)-dione, methyl 4-amino-3-chloro-6-(4- chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxyl ate, 2-methyl-3- (methylsulfonyl)-N-(l -methyl- lH-tetrazol-5-yl)-4-(trifluoromethyl)benzamide and 2-methyl- N-(4-methyl-l,2,5-oxadiazol-3-yl)-3-(methylsulfinyl)-4-(trif luoromethyl)benzamide. Other herbicides also include bioherbicides such as Alternaria destruens Simmons, Colletotrichum gloeosporiodes (Penz.) Penz. & Sacc, Drechsiera monoceras (MTB-951), Myrothecium verrucaria (Albertini & Schweinitz) Ditmar: Fries, Phytophthora palmivora (Butl.) Butl. and Puccinia thlaspeos Schub.

Compounds of this invention can also be used in combination with plant growth regulators such as avi glycine, N-(phenylmethyl)-lH-purin-6-amine, epocholeone, gibberellic acid, gibberellin A ₄ and A ₇ , harpin protein, mepiquat chloride, prohexadione calcium, prohydrojasmon, sodium nitrophenolate and trinexapac-methyl, and plant growth modifying organisms such as Bacillus cereus strain BP01.

General references for agricultural protectants (i.e. herbicides, herbicide safeners, 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 the amounts similar to amounts customary when the mixture partners are used alone. More particularly in mixtures, active ingredients are often applied at an application rate between one-half and the full application rate specified on product labels for use of active ingredient alone. 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 1 is typically between about 1 :3000 and about 3000: 1. Of note are weight ratios between about 1 :300 and about 300: 1 (for example ratios between about 1 :30 and about 30: 1). One skilled in the art can easily determine through simple experimentation the biologically effective amounts of active ingredients necessary for the desired spectrum of biological activity. It will be evident that including these additional components may expand the spectrum of weeds controlled beyond the spectrum controlled by the compound of Formula 1 alone.

In certain instances, combinations of a compound of this invention with other biologically active (particularly herbicidal) compounds or agents (i.e. active ingredients) can result in a greater-than-additive (i.e. synergistic) effect on weeds and/or a less-than-additive effect (i.e. safening) on crops or other desirable plants. Reducing the quantity of active ingredients released in the environment while ensuring effective pest control is always desirable. Ability to use greater amounts of active ingredients to provide more effective weed control without excessive crop injury is also desirable. When synergism of herbicidal active ingredients occurs on weeds at application rates giving agronomically satisfactory levels of weed control, such combinations can be advantageous for reducing crop production cost and decreasing environmental load. When safening of herbicidal active ingredients occurs on crops, such combinations can be advantageous for increasing crop protection by reducing weed competition.

Of note is a combination of a compound of the invention with at least one other herbicidal active ingredient. Of particular note is such a combination where the other herbicidal active ingredient has different site of action from the compound of the invention. In certain instances, a combination with at least one other herbicidal active ingredient having a similar spectrum of control but a different site of action will be particularly advantageous for resistance management. Thus, a composition of the present invention can 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 invention can also be used in combination with herbicide safeners such as allidochlor, benoxacor, cloquintocet-mexyl, cumyluron, cyometrinil, cyprosulfonamide, daimuron, dichlormid, dicyclonon, dietholate, dimepiperate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpyr- di ethyl, mephenate, methoxyphenone naphthalic anhydride (1,8-naphthalic anhydride), oxabetrinil, N-(aminocarbonyl)-2-methylbenzenesulfonamide, N-(aminocarbonyl)- 2-fluorobenzenesulfonamide, l-bromo-4-[(chloromethyl)sulfonyl]benzene (BCS), 4- (dichloroacetyl)-l-oxa-4-azospiro[4.5]decane (MON 4660), 2-(dichloromethyl)-2-methyl- 1,3-dioxolane (MG 191), ethyl l,6-dihydro-l-(2-methoxyphenyl)-6-oxo-2-phenyl-5- pyrimidinecarboxylate, 2-hydroxy-N,N-dimethyl-6-(trifluoromethyl)pyridine-3- carboxamide, and 3-oxo-l-cyclohexen-l-yl l-(3,4-dimethylphenyl)-l,6-dihydro-6-oxo-2- phenyl-5-pyrimidinecarboxylate, 2,2-dichloro-l-(2,2,5-trimethyl-3-oxazolidinyl)-ethanone and 2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfony l]-benzamide to increase safety to certain crops. Antidotally effective amounts of the herbicide safeners can be applied at the same time as the compounds of this invention, or applied as seed treatments. Therefore an aspect of the present invention relates to a herbicidal mixture comprising a compound of this invention and an antidotally effective amount of a herbicide safener. Seed treatment is particularly useful for selective weed control, because it physically restricts antidoting to the crop plants. Therefore a particularly useful embodiment of the present invention is a method for selectively controlling the growth of undesired vegetation in a crop comprising contacting the locus of the crop with a herbicidally effective amount of a compound of this invention wherein seed from which the crop is grown is treated with an antidotally effective amount of safener. Antidotally effective amounts of safeners can be easily determined by one skilled in the art through simple experimentation.

Compounds of the invention cans also be mixed with: (1) polynucleotides including but not limited to DNA, RNA, and/or chemically modified nucleotides influencing the amount of a particular target through down regulation, interference, suppression or silencing of the genetically derived transcript that render a herbicidal effect; or (2) polynucleotides including but not limited to DNA, RNA, and/or chemically modified nucleotides influencing the amount of a particular target through down regulation, interference, suppression or silencing of the genetically derived transcript that render a safening effect.

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 herbicide safeners (in an effective amount), and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents.

Preferred for better control of undesired vegetation (e.g., lower use rate such as from synergism, broader spectrum of weeds controlled, or enhanced crop safety) or for preventing the development of resistant weeds are mixtures of a compound of this invention with a herbicide selected from the group 2,4-D, acetochlor, alachlor, atrazine, bromoxynil, bentazon, bicyclopyrone, carfentrazone-ethyl, cloransulam-methyl, dicamba, dimethenamid- p, florasulam, flufenacet, flumioxazin, flupyrsulfuron-methyl, fluroxypyr-meptyl, glyphosate, halauxifen-methyl, isoxaflutole, MCPA, mesotrione, metolachlor, metsulfuron- methyl, nicosulfuron, pyrasulfotole, pyroxasulfone, pyroxsulam, rimsulfuron, saflufenacil, tembotrione, thifensulfuron-methyl, topramazone and tribenuron.

Table Al lists specific combinations of a Component (a) with Component (b) illustrative of the mixtures, compositions and methods of the present invention. Compound 13 in the Component (a) column is identified in Index Table A. The second column of Table Al lists the specific Component (b) compound (e.g., "2,4-D" in the first line). The third, fourth and fifth columns of Table Al lists 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 Al specifically discloses the combination of Component (a) (i.e. Compound 13 in Index Table A) with 2,4-D is typically applied in a weight ratio between 1:192 - 6:1. The remaining lines of Table Al are to be construed similarly.

TABLE Al

Component (a) Typical More Typical Most Typical (Compound 13) Component (b) Weight Ratio Weight Ratio Weight Ratio

13 2,4-D 1:192-6:1 1:64-2:1 1:24-1:3

13 Acetochlor 1:768-2:1 1:256- 1:2 1:96-1:11

13 Acifluorfen 1:96-12:1 1:32-4:1 1:12-1:2

13 Aclonifen 1:857-2:1 1:285 - 1:3 1:107-1:12

13 Alachlor 1:768-2:1 1:256- 1:2 1:96-1:11

13 Ametryn 1:384- 3:1 1:128-1:1 1:48-1:6

13 Amicarbazone 1:192-6:1 1:64-2:1 1:24-1:3

13 Amidosulfuron 1:6-168:1 1:2-56:1 1:1-11:1

13 Aminocyclopyrachlor 1:48-24:1 1:16-8:1 1:6-2:1

13 Aminopyralid 1:20-56:1 1:6-19:1 1:2-4:1

13 Amitrole 1:768-2:1 1:256- 1:2 1:96-1:11

13 Anilofos 1:96-12:1 1:32-4:1 1:12-1:2

13 Asulam 1:960-2:1 1:320- 1:3 1:120-1:14

13 Atrazine 1:192-6:1 1:64-2:1 1:24-1:3

13 Azimsulfuron 1:6-168:1 1:2-56:1 1:1-11:1

13 Beflubutamid 1:342-4:1 1:114-2:1 1:42-1:5

13 Benfuresate 1:617-2:1 1:205- 1:2 1:77-1:9

13 Bensulfuron-methyl 1:25 -45:1 1:8-15:1 1:3-3:1

13 Bentazone 1:192-6:1 1:64-2:1 1:24-1:3

13 Benzobicyclon 1:85-14:1 1:28-5:1 1:10-1:2

13 Benzofenap 1:257-5:1 1:85-2:1 1:32-1:4

13 Bicyclopyrone 1:42-27:1 1:14-9:1 1:5-2:1

13 Bifenox 1:257-5:1 1:85-2:1 1:32-1:4

13 Bispyribac-sodium 1:10-112:1 1:3-38:1 1:1-7:1

13 Bromacil 1:384- 3:1 1:128-1:1 1:48-1:6

13 Bromobutide 1:384 -3:1 1:128-1:1 1:48-1:6

13 Bromoxynil 1:96-12:1 1:32-4:1 1:12-1:2

13 Butachlor 1:768-2:1 1:256- 1:2 1:96-1:11

13 Butafenacil 1:42-27:1 1:14-9:1 1:5-2:1

13 Butylate 1:1542- 1:2 1:514-1:5 1:192-1:22

13 Carfenstrole 1:192-6:1 1:64-2:1 1:24-1:3

13 Carfentrazone-ethyl 1:128-9:1 1:42-3:1 1:16-1:2 Component (a) Typical More Typical Most Typical (Compound 13) Component (b) Weight Ratio Weight Ratio Weight Ratio

13 Chlorimuron-ethyl 1:8-135:1 1:2-45:1 1:1-9:1

13 Chlorotoluron 1:768-2:1 1:256- 1:2 1:96-1:11

13 Chlorsulfuron 1:6-168:1 1:2-56:1 1:1-11:1

13 Cincosulfuron 1:17-68:1 1:5-23:1 1:2-5:1

13 Cinidon-ethyl 1:384 -3:1 1:128-1:1 1:48-1:6

13 Cinmethylin 1:34-34:1 1:11 - 12:1 1:4-3:1

13 Clacyfos 1:34-34:1 1:11 - 12:1 1:4-3:1

13 Clethodim 1:48-24:1 1:16-8:1 1:6-2:1

13 Clodinafop-propargyl 1:20-56:1 1:6-19:1 1:2-4:1

13 Clomazone 1:384- 3:1 1:128-1:1 1:48-1:6

13 Clomeprop 1:171-7:1 1:57-3:1 1:21-1:3

13 Clopyralid 1:192-6:1 1:64-2:1 1:24-1:3

13 Cloransulam-methyl 1:12-96:1 1:4-32:1 1:1-6:1

13 Cumyluron 1:384- 3:1 1:128-1:1 1:48-1:6

13 Cyanazine 1:384- 3:1 1:128-1:1 1:48-1:6

13 Cyclopyrimorate 1:17-68:1 1:5-23:1 1:2-5:1

13 Cyclosulfamuron 1:17-68:1 1:5-23:1 1:2-5:1

13 Cycloxydim 1:96-12:1 1:32-4:1 1:12-1:2

13 Cyhalofop 1:25 -45:1 1:8-15:1 1:3-3:1

13 Daimuron 1:192-6:1 1:64-2:1 1:24-1:3

13 Desmedipham 1:322-4:1 1:107-2:1 1:40-1:5

13 Dicamba 1:192-6:1 1:64-2:1 1:24-1:3

13 Dichlobenil 1:1371 - 1:2 1:457- 1:4 1:171-1:20

13 Dichlorprop 1:925 -2:1 1:308- 1:3 1:115-1:13

13 Diclofop-methyl 1:384- 3:1 1:128-1:1 1:48-1:6

13 Diclosulam 1:10-112:1 1:3-38:1 1:1-7:1

13 Difenzoquat 1:288-4:1 1:96-2:1 1:36-1:4

13 Diflufenican 1:857-2:1 1:285 - 1:3 1:107-1:12

13 Diflufenzopyr 1:12-96:1 1:4-32:1 1:1-6:1

13 Dimethachlor 1:768-2:1 1:256- 1:2 1:96-1:11

13 Dimethametryn 1:192-6:1 1:64-2:1 1:24-1:3

13 Dimethenamid-P 1:384- 3:1 1:128-1:1 1:48-1:6

13 Dithiopyr 1:192-6:1 1:64-2:1 1:24-1:3

13 Diuron 1:384- 3:1 1:128-1:1 1:48-1:6

13 EPTC 1:768-2:1 1:256- 1:2 1:96-1:11 Component (a) Typical More Typical Most Typical (Compound 13) Component (b) Weight Ratio Weight Ratio Weight Ratio

13 Esprocarb 1:1371 - 1:2 1:457- 1:4 1:171-1:20

13 Ethalfluralin 1:384- 3:1 1:128-1:1 1:48-1:6

13 Ethametsulfuron-methyl 1:17-68:1 1:5-23:1 1:2-5:1

13 Ethoxyfen 1:8-135:1 1:2-45:1 1:1-9:1

13 Ethoxysulfuron 1:20-56:1 1:6-19:1 1:2-4:1

13 Etobenzanid 1:257-5:1 1:85-2:1 1:32-1:4

13 Fenoxaprop-ethyl 1:120-10:1 1:40-4:1 1:15-1:2

13 Fenoxasulfone 1:85-14:1 1:28-5:1 1:10-1:2

13 Fenquinotrione 1:17-68:1 1:5-23:1 1:2-5:1

13 Fentrazamide 1:17-68:1 1:5-23:1 1:2-5:1

13 Flazasulfuron 1:17-68:1 1:5-23:1 1:2-5:1

13 Florasulam 1:2-420:1 1:1-140:1 2:1-27:1

13 Fluazifop-butyl 1:192-6:1 1:64-2:1 1:24-1:3

13 Flucarbazone 1:8-135:1 1:2-45:1 1:1-9:1

13 Flucetosulfuron 1:8-135:1 1:2-45:1 1:1-9:1

13 Flufenacet 1:257-5:1 1:85-2:1 1:32-1:4

13 Flumetsulam 1:24-48:1 1:8-16:1 1:3-3:1

13 Flumiclorac-pentyl 1:10-112:1 1:3-38:1 1:1-7:1

13 Flumioxazin 1:25 -45:1 1:8-15:1 1:3-3:1

13 Fluometuron 1:384- 3:1 1:128-1:1 1:48-1:6

13 Flupyrsulfuron-methyl 1:3 -336:1 1:1-112:1 2:1-21:1

13 Fluridone 1:384- 3:1 1:128-1:1 1:48-1:6

13 Fluroxypyr 1:96-12:1 1:32-4:1 1:12-1:2

13 Flurtamone 1:857-2:1 1:285- 1:3 1:107-1:12

13 Fluthiacet-methyl 1:48-42:1 1:16-14:1 1:3-3:1

13 Fomesafen 1:96-12:1 1:32-4:1 1:12-1:2

13 Foramsulfuron 1:13-84:1 1:4-28:1 1:1-6:1

13 Glufosinate 1:288-4:1 1:96-2:1 1:36-1:4

13 Glyphosate 1:288-4:1 1:96-2:1 1:36-1:4

13 Halosulfuron-methyl 1:17-68:1 1:5-23:1 1:2-5:1

13 Halauxifen 1:20-56:1 1:6-19:1 1:2-4:1

13 Halauxifen methyl 1:20-56:1 1:6-19:1 1:2-4:1

13 Haloxyfop-methyl 1:34-34:1 1:11 - 12:1 1:4-3:1

13 Hexazinone 1:192-6:1 1:64-2:1 1:24-1:3

13 Hydantocidin 1:1100-16:1 1:385 - 8:1 1:144-4:1 Component (a) Typical More Typical Most Typical (Compound 13) Component (b) Weight Ratio Weight Ratio Weight Ratio

13 Imazamox 1:13-84:1 1:4-28:1 1:1-6:1

13 Imazapic 1:20-56:1 1:6-19:1 1:2-4:1

13 Imazapyr 1:85-14:1 1:28-5:1 1:10-1:2

13 Imazaquin 1:34-34:1 1:11-12:1 1:4-3:1

13 Imazethabenz -methyl 1:171-7:1 1:57-3:1 1:21-1:3

13 Imazethapyr 1:24-48:1 1:8-16:1 1:3-3:1

13 Imazosulfuron 1:27-42:1 1:9-14:1 1:3-3:1

13 Indanofan 1:342-4:1 1:114-2:1 1:42-1:5

13 Indaziflam 1:25-45:1 1:8-15:1 1:3-3:1

13 Iodosulfuron-methyl 1:3 -336:1 1:1-112:1 2:1-21:1

13 Ioxynil 1:192-6:1 1:64-2:1 1:24-1:3

13 Ipfencarbazone 1:85-14:1 1:28-5:1 1:10-1:2

13 Isoproturon 1:384 -3:1 1:128-1:1 1:48-1:6

13 Isoxaben 1:288-4:1 1:96-2:1 1:36-1:4

13 Isoxaflutole 1:60-20:1 1:20-7:1 1:7-2:1

13 Lactofen 1:42-27:1 1:14-9:1 1:5-2:1

13 Lenacil 1:384- 3:1 1:128-1:1 1:48-1:6

13 Linuron 1:384- 3:1 1:128-1:1 1:48-1:6

13 MCPA 1:192-6:1 1:64-2:1 1:24-1:3

13 MCPB 1:288-4:1 1:96-2:1 1:36-1:4

13 Mecoprop 1:768-2:1 1:256- 1:2 1:96-1:11

13 Mefenacet 1:384- 3:1 1:128-1:1 1:48-1:6

13 Mefluidide 1:192-6:1 1:64-2:1 1:24-1:3

13 Mesosulfuron-methyl 1:5-224:1 1:1-75:1 1:1-14:1

13 Mesotrione 1:42-27:1 1:14-9:1 1:5-2:1

13 Metamifop 1:42-27:1 1:14-9:1 1:5-2:1

13 Metazachlor 1:384 -3:1 1:128-1:1 1:48-1:6

13 Metazosulfuron 1:25-45:1 1:8-15:1 1:3-3:1

13 Methabenzthiazuron 1:768-2:1 1:256- 1:2 1:96-1:11

13 Metolachlor 1:768-2:1 1:256- 1:2 1:96-1:11

13 Metosulam 1:8-135:1 1:2-45:1 1:1-9:1

13 Metribuzin 1:192-6:1 1:64-2:1 1:24-1:3

13 Metsulfuron-methyl 1:2-560:1 1:1 - 187:1 3:1-35:1

13 Molinate 1:1028-2:1 1:342- 1:3 1:128-1:15

13 Napropamide 1:384 -3:1 1:128-1:1 1:48-1:6 Component (a) Typical More Typical Most Typical (Compound 13) Component (b) Weight Ratio Weight Ratio Weight Ratio

13 Napropamide-M 1:192-6:1 1:64-2:1 1:24-1:3

13 Naptalam 1:192-6:1 1:64-2:1 1:24-1:3

13 Nicosulfuron 1:12-96:1 1:4-32:1 1:1-6:1

13 Norflurazon 1:1152-1:1 1:384- 1:3 1:144-1:16

13 Orbencarb 1:1371 - 1:2 1:457- 1:4 1:171-1:20

13 Orthosulfamuron 1:20-56:1 1:6-19:1 1:2-4:1

13 Oryzalin 1:514-3:1 1:171-1:2 1:64-1:8

13 Oxadiargyl 1:384 -3:1 1:128-1:1 1:48-1:6

13 Oxadiazon 1:548-3:1 1:182-1:2 1:68-1:8

13 Oxasulfuron 1:27-42:1 1:9-14:1 1:3-3:1

13 Oxaziclomefone 1:42-27:1 1:14-9:1 1:5-2:1

13 Oxyfluorfen 1:384- 3:1 1:128-1:1 1:48-1:6

13 Paraquat 1:192-6:1 1:64-2:1 1:24-1:3

13 Pendimethalin 1:384- 3:1 1:128-1:1 1:48-1:6

13 Penoxsulam 1:10-112:1 1:3-38:1 1:1-7:1

13 Penthoxamid 1:384- 3:1 1:128-1:1 1:48-1:6

13 Pentoxazone 1:102-12:1 1:34-4:1 1:12-1:2

13 Phenmedipham 1:102-12:1 1:34-4:1 1:12-1:2

13 Picloram 1:96-12:1 1:32-4:1 1:12-1:2

13 Picolinafen 1:34-34:1 1:11 - 12:1 1:4-3:1

13 Pinoxaden 1:25 -45:1 1:8-15:1 1:3-3:1

13 Pretilachlor 1:192-6:1 1:64-2:1 1:24-1:3

13 Primisulfuron-methyl 1:8-135:1 1:2-45:1 1:1-9:1

13 Prodiamine 1:384- 3:1 1:128-1:1 1:48-1:6

13 Profoxydim 1:42-27:1 1:14-9:1 1:5-2:1

13 Prometryn 1:384- 3:1 1:128-1:1 1:48-1:6

13 Propachlor 1:1152-1:1 1:384- 1:3 1:144-1:16

13 Propanil 1:384- 3:1 1:128-1:1 1:48-1:6

13 Propaquizafop 1:48-24:1 1:16-8:1 1:6-2:1

13 Propoxycarbazone 1:17-68:1 1:5-23:1 1:2-5:1

13 Propyrisulfuron 1:17-68:1 1:5-23:1 1:2-5:1

13 Propyzamide 1:384- 3:1 1:128-1:1 1:48-1:6

13 Prosulfocarb 1:1200- 1:2 1:400- 1:4 1:150-1:17

13 Prosulfuron 1:6-168:1 1:2-56:1 1:1-11:1

13 Pyraclonil 1:42-27:1 1:14-9:1 1:5-2:1 Component (a) Typical More Typical Most Typical (Compound 13) Component (b) Weight Ratio Weight Ratio Weight Ratio

13 Pyraflufen-ethyl 1:5-224:1 1:1-75:1 1:1-14:1

13 Pyrasulfotole 1:13-84:1 1:4-28:1 1:1-6:1

13 Pyrazolynate 1:857-2:1 1:285 - 1:3 1:107-1:12

13 Pyrazosulfuron-ethyl 1:10-112:1 1:3-38:1 1:1-7:1

13 Pyrazoxyfen 1:5-224:1 1:1-75:1 1:1-14:1

13 Pyribenzoxim 1:10-112:1 1:3-38:1 1:1-7:1

13 Pyributicarb 1:384- 3:1 1:128-1:1 1:48-1:6

13 Pyridate 1:288-4:1 1:96-2:1 1:36-1:4

13 Pyriftalid 1:10-112:1 1:3-38:1 1:1-7:1

13 Pyriminobac -methyl 1:20-56:1 1:6-19:1 1:2-4:1

13 Pyrimisulfan 1:17-68:1 1:5-23:1 1:2-5:1

13 Pyrithiobac 1:24-48:1 1:8-16:1 1:3-3:1

13 Pyroxasulfone 1:85-14:1 1:28-5:1 1:10-1:2

13 Pyroxsulam 1:5-224:1 1:1-75:1 1:1-14:1

13 Quinclorac 1:192-6:1 1:64-2:1 1:24-1:3

13 Quizalofop-ethyl 1:42-27:1 1:14-9:1 1:5-2:1

13 Rimsulfuron 1:13-84:1 1:4-28:1 1:1-6:1

13 Saflufenacil 1:25-45:1 1:8-15:1 1:3-3:1

13 Sethoxydim 1:96-12:1 1:32-4:1 1:12-1:2

13 Simazine 1:384- 3:1 1:128-1:1 1:48-1:6

13 Sulcotrione 1:120-10:1 1:40-4:1 1:15-1:2

13 Sulfentrazone 1:147-8:1 1:49-3:1 1:18-1:3

13 Sulfometuron-methyl 1:34-34:1 1:11 - 12:1 1:4-3:1

13 Sulfosulfuron 1:8-135:1 1:2-45:1 1:1-9:1

13 Tebuthiuron 1:384- 3:1 1:128-1:1 1:48-1:6

13 Tefuryltrione 1:42-27:1 1:14-9:1 1:5-2:1

13 Tembotrione 1:31-37:1 1:10-13:1 1:3-3:1

13 Tepraloxydim 1:25-45:1 1:8-15:1 1:3-3:1

13 Terbacil 1:288-4:1 1:96-2:1 1:36-1:4

13 Terbuthylazine 1:857-2:1 1:285- 1:3 1:107-1:12

13 Terbutryn 1:192-6:1 1:64-2:1 1:24-1:3

13 Thenylchlor 1:85-14:1 1:28-5:1 1:10-1:2

13 Thiazopyr 1:384- 3:1 1:128-1:1 1:48-1:6

13 Thiencarbazone 1:3 -336:1 1:1-112:1 2:1-21:1

13 Thifensulfuron-methyl 1:5-224:1 1:1-75:1 1:1-14:1 Component (a) Typical More Typical Most Typical (Compound 13) Component (b) Weight Ratio Weight Ratio Weight Ratio

13 Tiafenacil 1:17-68:1 1:5-23:1 1:2-5:1

13 Thiobencarb 1:768-2:1 1:256- 1:2 1:96-1:11

13 Tolpyralate 1:31-37:1 1:10-13:1 1:3-3:1

13 Topramzone 1:6-168:1 1:2-56:1 1:1-11:1

13 Tralkoxydim 1:68-17:1 1:22-6:1 1:8-2:1

13 Triafamone 1:2-420:1 1:1-140:1 2:1-27:1

13 Triallate 1:768-2:1 1:256- 1:2 1:96-1:11

13 Triasulfuron 1:5-224:1 1:1-75:1 1:1-14:1

13 Triaziflam 1:171-7:1 1:57-3:1 1:21-1:3

13 Tribenuron-methyl 1:3 -336:1 1:1-112:1 2:1-21:1

13 Triclopyr 1:192-6:1 1:64-2:1 1:24-1:3

13 Trifloxysulfuron 1:2-420:1 1:1-140:1 2:1-27:1

13 Trifludimoxazin 1:25-45:1 1:8-15:1 1:3-3:1

13 Trifluralin 1:288-4:1 1:96-2:1 1:36-1:4

13 Triflusulfuron-methyl 1:17-68:1 1:5-23:1 1:2-5:1

13 Tritosulfuron 1:13-84:1 1:4-28:1 1:1-6:1

Table A2 is constructed the same as Table Al above except that entries below the "Component (a)" column heading are replaced with the respective Component (a) Column Entry shown below. Compound 15 in the Component (a) column is identified in Index Table A. Thus, for example, in Table A2 the entries below the "Component (a)" column heading all recite "Compound 15" (i.e. Compound 15 identified in Index Table A), and the first line below the column headings in Table A2 specifically discloses a mixture of Compound 15 with 2,4-D. Tables A3 through A146 are constructed similarly.

Table Number Component (a) Column Entries Table Number Component (a) Column Entries

A2 Compound 15 A13 Compound 5

A3 Compound 16 A14 Compound 6

A4 Compound 21 A15 Compound 7

A5 Compound 22 A16 Compound 8

A6 Compound 23 A17 Compound 9

A7 Compound 24 A18 Compound 10

A8 Compound 27 A19 Compound 11

A9 Compound 1 A20 Compound 12

A10 Compound 2 A21 Compound 14

All Compound 3 A22 Compound 17

A12 Compound 4 A23 Compound 18 '3

Table Number Component (a) Column Entries Table Number Component (a) Column Entries

A24 Compound 19 A61 Compound 61

A25 Compound 20 A62 Compound 62

A26 Compound 25 A63 Compound 63

A27 Compound 26 A64 Compound 64

A28 Compound 28 A65 Compound 65

A29 Compound 29 A66 Compound 66

A30 Compound 30 A67 Compound 67

A31 Compound 31 A68 Compound 68

A32 Compound 32 A69 Compound 69

A33 Compound 33 A70 Compound 70

A34 Compound 34 A71 Compound 71

A35 Compound 35 A72 Compound 72

A36 Compound 36 A73 Compound 73

A37 Compound 37 A74 Compound 74

A38 Compound 38 A75 Compound 75

A39 Compound 39 A76 Compound 76

A40 Compound 40 A77 Compound 77

A41 Compound 41 A78 Compound 78

A42 Compound 42 A79 Compound 79

A43 Compound 43 A80 Compound 80

A44 Compound 44 A81 Compound 81

A45 Compound 45 A82 Compound 82

A46 Compound 46 A83 Compound 83

A47 Compound 47 A84 Compound 84

A48 Compound 48 A85 Compound 85

A49 Compound 49 A86 Compound 86

A50 Compound 50 A87 Compound 87

A51 Compound 51 A88 Compound 88

A52 Compound 52 A89 Compound 89

A53 Compound 53 A90 Compound 90

A54 Compound 54 A91 Compound 91

A55 Compound 55 A92 Compound 92

A56 Compound 56 A93 Compound 93

A57 Compound 57 A94 Compound 94

A58 Compound 58 A95 Compound 95

A59 Compound 59 A96 Compound 96

A60 Compound 60 A97 Compound 97 Table Number Component (a) Column Entries Table Number Component (a) Column Entries

A98 Compound 98 A123 Compound 123

A99 Compound 99 A124 Compound 124

A100 Compound 100 A125 Compound 125

A101 Compound 101 A126 Compound 126

A102 Compound 102 A127 Compound 127

A103 Compound 103 A128 Compound 128

A104 Compound 104 A129 Compound 129

A105 Compound 104 A130 Compound 130

A106 Compound 106 A131 Compound 131

A107 Compound 107 A132 Compound 132

A108 Compound 108 A133 Compound 133

A109 Compound 109 A134 Compound 134

A110 Compound 110 A135 Compound 135

Al l l Compound 111 A136 Compound 136

A112 Compound 112 A137 Compound 137

A113 Compound 113 A138 Compound 138

A114 Compound 114 A139 Compound 139

A115 Compound 115 A140 Compound 140

A116 Compound 116 A141 Compound 141

A117 Compound 117 A142 Compound 142

A118 Compound 118 A143 Compound 143

A119 Compound 119 A144 Compound 144

A120 Compound 120 A145 Compound 145

A121 Compound 121 A146 Compound 146

A122 Compound 122

The compounds of the present invention are useful for the control of weed species that are resistant to herbicides with the AHAS-inhibitor or (b2) [chemical compound that inhibits acetohydroxy acid synthase (AHAS), also known as acetolactate synthase (ALS)] mode of action.

The following Tests demonstrate the control efficacy of the compounds of this invention against specific weeds. The weed control afforded by the compounds is not limited, however, to these species. See Index Tables A-C for compound descriptions. The following abbreviations are used in the Index Tables which follow: t is tertiary, s is secondary, n is normal, i is iso, c is cyclo, Me is methyl, Et is ethyl, Pr is propyl, z ^' -Pr is isopropyl, Bu is butyl, c-Pr is cyclopropyl, t-Bu is tert-butyl, Ph is phenyl, OMe is methoxy, OEt is ethoxy, SMe is methylthio, TFP is trifluoropropyl (i.e. -CH ₂ CH ₂ CF3), Bn is benzyl and -CN is cyano. The abbreviation "Cmpd. No." stands for "Compound Number". The abbreviation "Ex." stands for "Example" and is followed by a number indicating in which example the compound is prepared. Mass spectra are reported with an estimated precision within ±0.5 Da as the molecular weight of the highest isotopic abundance parent ion (M+1) formed by addition of H ⁺ (molecular weight of 1) to the molecule. The presence of molecular ions containing one or more higher atomic weight isotopes of lower abundance (e.g., ³⁷ C1, ⁸¹ Br) is not reported. The alternate molecular ion peaks (e.g., M+2 or M+4) that occur with compounds containing multiple halogens are not reported. The reported M+1 peaks were observed by mass spectrometry using atmospheric pressure chemical ionization (AP ⁺ ) or electrospray ionization (ESI).

A-l A-2 A-3A A-5 A-7

M.S.(AP+)

Cmpd. No. A Rl R2 R3 or m.p.

1 A-3A OCH ₂ CH(CH ₃ ) ₂ CI 3 -Br *

2 A-3A 0CH ₂ C(C1)=CH ₂ CI 3 -Br *

3 A-3A OCH ₂ C(CH ₃ )=CH ₂ CI 3 -Br *

4 A-3A OCH ₂ CF ₂ CF ₃ Br 3-F 447

5 A-3A OCH ₂ CF ₂ CF ₃ CI 3-F 401

6 A-3A OCH ₂ (cyclo-pent l) CI 3 -Br 411

7 A-3A OCH ₂ CH ₂ CN CI 3 -Br 382

8 A-3A OCH ₂ (cyclo-butyl) CI 3 -Br 397

9 A-3A OCH ₂ (cyclo-propyl) CI 3 -Br 393

10 A-3A OCH ₂ (2,2-di-F-cyclo-propyl) CI 3 -Br 419

11 A-3A OCH ₂ CH=C(CH ₃ ) ₂ CI 3 -Br 397

12 A-3A CH ₃ CI 3 -Br * M.S.(AP+)

Cmpd. No. A Rl R2 R3 or m.p.

13 A-3A OCH ₂ CH ₂ CH ₃ CI 3 -Br *

14 A-3A OC(CH ₃ ) ₃ CI 3 -Br *

15 A-3A OCH ₂ CH ₂ CF ₃ CI 3 -CI 381

16 A-3A OCH(CH ₃ )CH ₂ CF ₃ CI 3 -Br 439

17 A-3A OCH ₂ CH ₂ CF ₃ CI (m = 0) 347

18 A-3A N(CH ₃ )CH ₂ CH(CH ₃ )(CF ₃ ) CI 3 -Br 452

19 A-3A N(CH ₃ )CH ₂ CH ₂ CF ₃ CI 3 -Br 438

20 A-3A OCH ₂ CH ₂ CH ₂ CF ₃ CI 3 -Br *

21 (Ex. 2) A-3A OCH ₂ CH ₂ CH=CH ₂ CI 3 -Br *

22 A-3A OCH ₂ CH=CH ₂ CI 3 -Br 369

23 A-3A OCH ₂ CF ₂ CF ₃ CI 3 -Br 461

24 A-3A N(CH ₃ )OCH ₂ CF ₃ Br 3 -Br 484

25 A-3A N(CH ₃ )OCH ₂ CF ₃ CI 3 -Br 440

26 (Ex. 3) A-3A OCH ₂ CH ₂ CF ₃ CI 3 -Br 425

27 A-3A NHCH ₂ CF ₃ Br (m = 0) *

28 (Ex. 1) A-3A NHCH ₂ CF ₃ CI (m = 0) *

29 A-3A CH ₂ C1 CI (m = 0) 283 (65-70)

30 A-3A OCH ₂ CH ₂ CF ₃ CI 3-CN 372

31 A-3A OCH ₂ CF ₃ CN 3 -Br *

32 A-3A OCH ₂ CF ₃ CI 3-CN 358

33 A-3A OCH ₂ CH ₂ CF ₃ Br 3 -Br 467

34 A-3A OCH ₂ CF ₃ Br 3 -Br 455

35 A-3A OCH ₂ CF ₃ CI 3 -Br 411

36 A-3A 0CH(CH ₂ C1) ₂ CI 3 -Br 439

37 A-3A OCH ₂ CH(CH ₃ )CH=CH ₂ CI 3 -Br 397

38 A-3A OCH ₂ CH ₂ C≡CH CI 3 -Br 381

39 A-3A OCH ₂ CN CI 3-CN 315

40 A-3A OCH ₂ CN CI 3 -Br *

41 A-3A OCH ₂ CH ₂ CF ₃ Br 3-F 409

42 A-3A OCH ₂ CH ₂ CF ₃ CI 3-F 365

43 A-3A OC(CH ₃ ) ₃ CI 3-F 325

44 A-3A O(cyclo-pentyl) CI 3 -Br 397

45 A-3A 0CH ₂ CC1 ₃ CI 3 -Br 459

46 A-3A 0CH ₂ CH ₂ C1 CI 3 -Br 391

47 A-3A OCH ₂ CF ₃ Br 3-F 396

48 A-3A OCH ₂ CF ₃ CI 3-F 351 M.S.(AP+)

Cmpd. No. A Rl R2 R3 or m.p.

49 A-3A OCH ₂ CN CI 3-F 308 (80-83)

50 A-3A £-OCH ₂ CH=CHCF ₃ CI 3 -Br 437

51 A-3A CH ₃ CI 3-OMe 279

52 A-3A CH ₃ CI (m = 0) 249

55 A-5; R ⁵ is Me CH ₃ CI (m = 0) 278

56 A-5; R ⁵ is i-Pr CH ₃ CI (m = 0) 306

57 A-5; R ⁵ is i-Pr H CI (m = 0) 292

58 A-5; R ⁵ is Bn CH ₃ CI (m = 0) 354

59 A-5; R ⁵ is t-Bu CH ₃ CI (m = 0) 320

60 A-5; R ⁵ is H CH ₃ CI (m = 0) 264

61 A-3A OCH ₂ C(Br)=CH ₂ CI 3 -Br 87-91

62 A-l OCH ₂ CF ₃ CI 3 -Br 63-66

63 A-l OCH ₂ CF ₂ CF ₃ CI 3 -Br 49-53

64 A-3A OCH ₂ CH ₂ CF ₃ CI 4-CN 117-120

65 A-3A OCH ₂ CH ₂ CH ₂ CF ₃ CI 3-CF ₃ 429

66 A-l OCH ₂ CH ₂ CF ₃ CI 3 -Br 63-67

67 A-3A CH ₂ CH ₂ CH ₃ CI 3-CN 85-88

68 A-3A CH ₂ CH ₂ CH ₂ CH ₃ CI 3-CN 98-102

69 A-5; R ⁵ is i-Pr CH ₃ CI 3-CN 80-84

70 A-3A SCH ₂ CH ₂ CH ₃ CI 3 -Br 387

71 A-3A SCH ₂ CH ₂ CF ₃ CI 3 -Br 121-125

72 A-l CH ₂ CH ₂ CF ₃ CI 3-CN 342

73 A-l (CH ₂ ) ₃ CF ₃ CI 3-CN 356

74 A-l 0(CH ₂ ) ₃ CF ₃ CI 3 -Br 425

75 A-3A CH ₂ CH ₂ CH ₃ CI 3 -Br 88-92

76 A-5; R ⁵ is i-Pr CH ₃ CI 3-F 62-66

77 A-3A (CH ₂ ) ₃ CF ₃ CI 3 -Br 423

78 A-3A O(c-Bu) CI 3 -Br 100-103

79 A-3A (CH ₂ ) ₃ CH ₃ CI 3 -Br 77-81

80 A-l 0(CH ₂ ) ₂ CF ₃ CI 3-CN 358

81 A-l 0(CH ₂ ) ₃ CF ₃ CI 3-CN 372

82 A-3A (CH ₂ ) ₄ CF ₃ CI 3 -Br 437

83 A-3A SCH ₂ CH ₃ CI 3 -Br 373

84 A-3A OCH(CH ₃ )CH ₂ CH ₃ CI 3 -Br 385

85 A-3A SCH ₂ CF ₃ CI 3 -Br 90-93

86 A-l (CH ₂ ) ₂ CH ₃ CI 3-CN 288 M.S.(AP+)

Cmpd. No. A Rl R2 R3 or m.p.

87 A-l (CH ₂ ) ₃ CH ₃ CI 3-CN 302

88 A-3A 0(CH ₂ ) ₂ CF ₃ CI 4-Cl 87-90

89 A-l (CH ₂ ) ₂ CF ₃ CI 3 -Br 395

90 A-3A OCH ₂ CH ₂ C(=CH ₂ )CH ₃ CI 3 -Br 397

91 A-3A SCH ₂ CH=CH ₂ CI 3-Br 385

92 A-3A (CH ₂ ) ₂ CF ₃ CI 3 -Br 409

93 A-3A NH(CH ₂ ) ₂ CF ₃ CI 3-Br 424

94 A-3A 0(CH ₂ ) ₂ CF ₃ CI 4-Br 88-91

95 A-5; R ⁵ is Et CH ₃ CI 3-Br 370

96 A-3A 0(CH ₂ ) ₂ C(CH ₃ ) ₃ CI 3-Br 413

97 A-3A 0CH ₂ CHC1CH ₂ C1 CI 3-Br 439

98 A-5; R ⁵ is TFP CH ₃ CI 3-Br *

99 A-3A 0(CH ₂ ) ₂ CF ₃ CI 3-CH ₃ 51-53

100 A-3A 0(CH ₂ ) ₃ CH ₃ CI 3-Br 385

101 A-3A 0(CH ₂ ) ₄ CH ₃ CI 3-Br 399

102 A-3A OCH ₂ CH ₂ CH ₂ CH ₂ Br CI 3-Br 449

103 A-3A OCH ₂ CF ₂ CHF ₂ CI 3-Br 443

104 A-5; R ⁵ is ; ^' -Pr CH ₃ CI 3 -CI 340

105 A-5; R ⁵ is /-Pr CH ₃ CI 3-Br 384

106 A-l OCH ₂ CH ₃ CI 3-Br 343

107 (Ex. 4) A-3A (CH ₂ ) ₂ CF ₃ CI 3 -CI **

108 A-3A OCH ₂ C≡CH CI 3-Br 108-112

109 A-3A (CH ₂ ) ₄ CF ₃ CI 3-CN 384

110 A-3A CH ₂ CH ₂ CF ₂ CF ₃ CI 3-Br 459

111 A-3A CH ₂ CH ₂ CF ₂ CF ₃ CI 3-CN 406

112 A-3A 0(CH ₂ ) ₂ CF ₃ CI 3-OCH ₃ 109-113

113 A-3A 0(CH ₂ ) ₂ CF ₃ CI 3-CF ₃ 415

114 A-2 (CH ₂ ) ₃ CH ₃ CI 3-Br 380

115 A-3A 0(CH ₂ ) ₂ CF ₃ CI 3-0-/-Pr 405

116 A-3A 0(CH ₂ ) ₂ CF ₃ CI 3-OCH ₂ CH ₃ 391

117 A-3A 0(CH ₂ ) ₂ CF ₃ CI 3-OCH ₂ CF ₃ 445

118 A-2 (CH ₂ ) ₂ CH ₃ CI 3-Br 366

121 A-l (CH ₂ ) ₄ CF ₃ CI 3-Br 423

122 A-l (CH ₂ ) ₂ CF ₃ CI 3 -CI 351 M.S.(AP+)

Cmpd. No. A Rl R2 R3 or m.p.

123 A-3A 0(CH ₂ ) ₂ c-Pr CI 3 -Br 397

124 A-l (CH ₂ ) ₄ CF ₃ CI 3 -CI 379

125 A-3A (CH ₂ ) ₃ CF ₃ CI 3-CF ₃ 413

126 A-7; R ¹⁵ is Me (CH ₂ ) ₃ CF ₃ CI 3-CN 371

127 A-3A cw-OCH ₂ C=C(CH ₃ )Cl CI 3 -Br 59-63

129 A-2 (CH ₂ ) ₃ CH ₃ CI (m = 0) 302

130 A-3A (CH ₂ ) ₃ CH ₃ CI 3-CF ₃ 359

131 A-l OCH ₂ CF ₃ CI 3-CN 344

132 A-l OCH ₂ CF ₂ CF ₃ CI 3-CN 70-73

133 A-3A (CH ₂ ) ₃ CF ₃ CI 3-CN 94-96

134 A-l (CH ₂ ) ₃ CF ₃ CI 3-CH ₂ CH ₃ 359

135 A-l (CH ₂ ) ₃ CF ₃ CI 3-c-Pr 371

136 A-3A (CH ₂ ) ₂ CH ₃ CI 3-CF ₃ 345

137 A-l (CH ₂ ) ₃ CF ₃ CI 3 -CI 365

138 A-l (CH ₂ ) ₃ CF ₃ CI 3 -Br 409

139 A-3A H CI 3 -CI *

140 A-2 H CI (m = 0) *

141 (Ex. 5) A-2 (CH ₂ ) ₄ CH ₃ CI (m = 0) **

142 A-3A (CH ₂ ) ₂ CF ₃ CI 3-CN 354

143 A-3A (CH ₂ ) ₃ CF ₃ CI 3 -CI 379

144 A-2 (CH ₂ ) ₃ CF ₃ CI (m = 0) 356

145 A-2 (CH ₂ ) ₄ CF ₃ CI (m = 0) 370

146 A-7; R ¹⁵ is H (CH ₂ ) ₃ CF ₃ CI 3-CN 358

* See Index Table C for ^: Η NMR data.

** See Synthesis Example for NMR data.

E indicates E stereochemistry of double bond INDEX TABLE B

M.S.(AP+)

INCode

Cmpd Structure or m.p.

INDEX TABLE C

Cmpd NMR (CDCI3 solution unless indicated otherwise)

1 8.48 (s, 2H), 7.53 (dd, IH), 7.35 (t, IH), 7.18 (dd, IH), 4.02 (d, 2H), 1.98-1.83 (m, IH), 0.89 (d, 6H).

8.48 (m, 2H), 7.55 (dd, IH), 7.38 (t, IH), 7.26 (s, IH), 7.20 (dd, IH), 5.55-5.46 (m, IH), 5.38 (m,

2

IH), 4.80-4.78 (m, 2H).

8.47 (s, 2H), 7.54 (dd, IH), 7.36 (t, IH), 7.19 (dd, IH), 4.99-4.93 (m, IH), 4.91-4.89 (m, IH), 4.63

3

(s, 2H), 1.71 (s, 3H).

12 8.48 (s, 2H), 7.51 (dd, IH), 7.32 (t, IH), 7.15 (dd, IH), 2.55 (s, 3H).

8.49 (s, 2H), 7.53 (dd, IH), 7.35 (t, IH), 7.18 (dd, IH), 4.20 (t, 2H), 1.58-1.67 (m, 2H), 0.82-0.93 13

(m, 3H).

14 8.49 (s, 2H), 7.51 (dd, 0.95 Hz, IH), 7.32 (t, IH), 7.16 (dd, IH), 1.43 (s, 9 H).

8.49 (s, 2H), 7.54 (dd, IH), 7.37 (t, IH), 7.20 (dd, IH), 4.31 (t, 2H), 2.20-2.04 (m, 2H), 1.93-1.85 20

(m, 2H).

8.48 (s, 2H), 7.53 (dd, IH), 7.35 (t, IH), 7.17 (dd, IH), 5.75-5.67 (m, IH), 5.09-5.05 (m, IH), 5.03-

21

5.00 (m, IH), 4.29 (t, 2H), 2.39-2.34 (m, 2H).

27 8.37 (s, 2H), 7.64 (d, IH), 7.46 (t, IH), 7.32 (t, IH), 7.19 (bs, IH), 7.00 (d, IH), 4.75 (q, 2H).

28 8.30 (s, 2H), 7.65 (d, IH), 7.48 (t, IH), 7.31 (t, IH), 7.21 (bs, IH), 7.00 (d, IH), 4.75 (q, 2H).

31 8.81 (s, 2H), 7.63 (dd, IH), 7.45 (t, IH), 7.22 (dd, IH), 4.58 (q, 2H).

40 8.50 (s, 2H), 7.57 (dd, IH), 7.43 (t, IH), 7.24 (dd, IH), 4.87 (s, 2H).

500 MHz) 8.47 (s, 2H) 7.53-7.56 (m, IH) 7.29-7.33 (m, IH) 7.14-7.18 (m, IH) 4.19 (t, 2H) 2.26-

99

2.36 (m, 2H) 2.09 (s, 3H).

139 10.39 (s, IH), 8.46 (s, 2H), 7.62-7.56 (m, IH), 7.47-7.42 (m, IH), 7.22-7.17 (m, IH). (500 MHz) 8.49 (s, 2H), 7.54-7.58 (m, 1H), 7.40-7.45 (m, 1H), 7.30-7.36 (m, 1H), 7.16-7.20 (m, 1H), 3.72 (s, 2H).

1H NMR data are in ppm downfield from tetramethylsilane. Couplings are designated by (s)-singlet, (d)-doublet, (t)-triplet, (m)-multiplet, (dd)-doublet of doublets, (dt)-doublet of triplets, (br s)-broad singlet

BIOLOGICAL EXAMPLES OF THE INVENTION

TEST A

Seeds of plant species selected from barnyardgrass (Echinochloa crus-galli), kochia (Kochia scoparid), ragweed (common ragweed, Ambrosia elatior), Italian ryegrass (Lolium multiflorum), large (Lg) crabgrass (Digitaria sanguinalis), giant foxtail (Setaria faberii), morningglory (Ipomoea spp.), pigweed (Amaranthus retroflexus), velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), and corn (Zea mays) were planted into a blend of loam soil and sand and treated preemergence with a directed soil spray using test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant.

At the same time, plants selected from these crop and weed species and also blackgrass (Alopecurus myosuroides), and galium (catchweed bedstraw, Galium aparine) were planted in pots containing the same blend of loam soil and sand and treated with postemergence applications of test chemicals formulated in the same manner. Plants ranged in height from 2 to 10 cm and were in the one- to two-leaf stage for the postemergence 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 evaluated for injury. Plant response ratings, summarized in Table A, are based on a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash (-) response means no test result.

Table A Compounds

1000 g ai/ha 12 55 56 57 58 59

Postemergence

Barnyardgrass 80 0 50 20 40 0

Blackgrass 50 - - - - -

Corn 20 0 30 20 30 20

Crabgrass, Large - 0 40 30 80 10

Foxtail, Giant 70 10 70 20 60 10

Galium 80 - - - - -

Kochia 80 - - - - -

Morningglory - - - 10 30 0

Pigweed 100 0 60 40 100 30

Ragweed 60 - - - - -

Ryegrass, Italian 50 - - - - - Velvetleaf - 10 100 - 90 -

Wheat 0 0 10 20 20 30

Table A Compounds

500 g ai/ha 6 7 8 9 10 11 13 14 15 16 17 18 20 21

Postemergence

Barnyardgrass 40 90 40 90 100 20 100 40 100 90 0 0 100 100

Blackgrass 30 80 20 80 90 20 70 70 100 90 0 0 50 80

Corn 10 70 20 50 60 10 90 10 90 60 20 0 40 60

Crabgrass, Large

Foxtail, Giant 50 100 60 90 100 20 100 60 100 90 0 0 100 100

Galium 90 100 90 100 100 20 100 100 100 100 0 0 90 90

Kochia 90 100 80 90 100 40 100 70 100 100 0 10 100 100

Morningglory

Pigweed 90 100 90 100 100 60 100 100 100 100 40 20 100 100

Ragweed 30 90 40 10 50 0 20 0 40 30 0 0 40 40

Ryegrass, Italian 40 70 30 50 60 0 100 70 90 30 0 0 40 90

Velvetleaf

Wheat 10 20 0 50 40 0 30 40 100 20 0 0 20 40

Table A Compounds

500 g ai/ha 22 23 24 25 26 27 28 30 31 32 33 34 35 39

Postemergence

Barnyardgrass 100 50 10 10 100 0 20 20 0 0 100 20 80 0

Blackgrass 90 50 0 30 100 - - 30 0 0 90 70 80 0

Corn 50 20 0 20 100 0 0 70 0 0 90 30 30 0

Crabgrass, Large - - - - - 0 0 - - - - - - -

Foxtail, Giant 100 80 0 10 100 0 0 100 0 0 100 80 100 0

Galium 90 100 20 50 100 - - 100 0 0 100 100 100 0

Kochia 100 100 0 50 100 - - 100 0 0 100 90 100 0

Morningglory - - - - - 0 0 - - - - - - -

Pigweed 100 100 10 60 100 0 20 100 0 30 100 100 100 0

Ragweed 30 10 0 20 60 - - 0 0 0 40 0 0 0

Ryegrass, Italian 60 70 0 0 80 - - 0 0 0 80 0 40 0

Velvetleaf - - - - - 0 30 - - - - - - -

Wheat 30 10 0 10 90 0 0 30 0 0 60 0 20 0

Table A Compounds

500 g ai/ha 40 41 42 47 48 49 61 64 65 72 73 75 78 79

Postemergence Barnyardgrass 20 0 0 0 30 0 100 0 70 100 100 100 100 100

Blackgrass 20 0 0 0 20 0 100 0 40 50 100 60 60 90

Corn 20 0 30 0 0 0 40 0 20 60 60 90 60 90

Crabgrass, Large

Foxtail, Giant 40 0 0 0 20 0 100 0 90 100 100 100 80 80

Galium 40 0 0 0 10 0 100 0 70 100 100 100 100 100

Kochia 100 60 60 0 0 0 - 0 - 100 100 100 100 100

Morningglory

Pigweed 100 90 90 0 40 0 100 0 100 100 100 100 90 100

Ragweed 0 10 0 0 0 0 30 0 30 30 30 40 30 40

Ryegrass, Italian 0 0 0 0 0 0 80 0 0 40 100 70 30 90

Velvetleaf

Wheat 20 0 0 0 0 0 30 0 0 40 90 70 30 30

Table A Compounds

500 g ai/ha 83 84 85 91 106 125 130 136 139

Postemergence

Barnyardgrass 90 40 20 100 100 90 100 80 0

Blackgrass 40 0 0 30 20 90 90 100 0

Corn 30 40 40 50 10 30 50 50 0

Crabgrass, Large

Foxtail, Giant 80 60 60 100 70 90 90 90 0

Galium 20 40 90 90 10 100 100 100 0

Kochia 90 70 80 100 - 100 100 100 0

Morningglory

Pigweed 70 70 70 100 20 100 100 100 0

Ragweed 0 0 0 20 0 40 60 60 0

Ryegrass, Italian 0 0 0 30 0 90 90 70 20

Velvetleaf

Wheat 0 20 20 30 0 30 30 20 0

Table A Compounds

125 g ai/ha 1 2 3 4 5 6 7 8 9 10 11 13 15 16

Postemergence

Barnyardgrass 30 40 60 0 0 10 30 10 20 20 10 80 90 10

Blackgrass 20 30 30 0 0 10 30 0 30 20 0 30 90 20

Corn 20 20 30 0 0 0 10 0 20 10 0 30 50 20

Foxtail, Giant 60 60 80 0 0 10 50 30 20 30 20 80 90 20

Galium 70 90 70 0 0 60 100 60 70 100 10 100 100 90 Kochia 30 90 40 0 0 40 100 40 50 90 0 100 100 80

Pigweed 70 80 100 0 0 60 100 50 100 90 10 90 100 90

Ragweed 10 0 0 0 0 10 40 10 0 10 0 0 20 10

Ryegrass, Italian 0 20 30 0 0 0 20 0 0 10 0 0 60 10

Wheat 0 0 0 0 0 0 0 0 10 0 0 20 20 20

Table A Compounds

125 g ai/ha 17 18 19 20 21 22 23 24 25 26 30 31 32 33

Postemergence

Barnyardgrass 0 0 0 30 70 60 10 0 0 100 0 0 0 80

Blackgrass 0 0 0 30 60 60 10 0 0 100 10 0 0 60

Corn 0 0 0 30 30 30 10 0 0 60 30 0 0 30

Foxtail, Giant 0 0 0 50 70 80 30 0 0 100 60 0 0 100

Galium 0 0 0 10 80 30 90 10 20 100 60 0 0 100

Kochia 0 0 0 90 90 90 80 0 10 100 100 0 0 100

Pigweed 20 10 10 100 80 100 100 0 30 100 100 0 20 100

Ragweed 0 0 0 0 0 0 0 0 10 30 0 0 0 30

Ryegrass, Italian 0 0 0 0 0 0 10 0 0 70 0 0 0 30

Wheat 0 0 0 0 0 0 0 0 0 40 0 0 0 20

Table A Compounds

125 g ai/ha 34 35 36 37 38 39 40 41 42 43 44 45 46 47

Postemergence

Barnyardgrass 0 10 0 30 60 0 0 0 0 10 0 20 30 0

Blackgrass 10 40 0 30 0 0 10 0 0 0 0 0 0 0

Corn 30 20 0 10 10 0 20 0 20 0 0 20 10 0

Foxtail, Giant 20 40 0 40 90 0 10 0 0 0 0 20 40 0

Galium 50 60 0 40 80 0 30 0 0 40 0 100 70 0

Kochia 60 90 0 40 60 0 70 20 30 10 0 50 90 0

Pigweed 100 100 60 80 100 0 70 90 80 40 0 100 100 0

Ragweed 0 0 0 0 10 0 0 0 0 0 0 10 0 0

Ryegrass, Italian 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Table A Compounds

125 g ai/ha 48 49 50 51 53 54 61 62 63 64 65 66 67 68

Postemergence

Barnyardgrass 0 0 20 0 0 0 100 40 10 0 30 100 0 30

Blackgrass 0 0 20 0 0 0 30 40 0 0 20 100 0 30

Corn 0 0 10 0 0 0 20 30 30 0 10 70 0 20 Foxtail, Giant 0 0 70 0 0 0 60 40 30 0 40 100 0 30

Galium 0 0 90 10 0 0 60 80 30 0 20 100 0 60

Kochia 0 0 90 0 0 0 - 100 50 0 - 50 0 40

Pigweed 20 0 100 0 0 0 40 90 60 0 90 100 0 90

Ragweed 0 0 0 0 0 0 10 0 0 0 10 20 0 20

Ryegrass, Italian 0 0 20 0 0 0 20 0 0 0 0 50 0 0

Wheat 0 0 0 0 0 0 0 0 0 0 0 30 0 0

Table A Compounds

125 g ai/ha 69 70 71 72 73 74 75 76 77 78 79 80 81 82

Postemergence

Barnyardgrass 70 30 40 80 90 40 90 0 90 60 90 90 50 100

Blackgrass 30 20 30 30 50 30 40 0 50 20 50 90 40 40

Corn 20 10 20 50 30 20 80 0 30 40 80 60 40 30

Foxtail, Giant 30 30 40 70 100 70 90 0 90 50 80 90 70 100

Galium 60 70 90 80 100 80 80 90 100 70 90 90 80 100

Kochia 40 70 50 100 100 40 100 0 100 70 100 70 50 100

Pigweed 80 20 70 100 100 100 100 30 100 80 100 100 100 100

Ragweed 0 20 20 10 20 10 30 0 0 0 30 30 10 40

Ryegrass, Italian 0 20 20 10 80 20 40 0 60 0 90 50 10 60

Wheat 0 0 0 10 20 10 20 0 10 20 20 40 0 30

Table A Compounds

125 g ai/ha 83 84 85 86 87 88 89 90 91 92 93 94 95 96

Postemergence

Barnyardgrass 0 0 0 40 100 0 90 30 30 100 0 0 30 10

Blackgrass 0 0 0 20 70 0 60 0 20 50 0 0 10 10

Corn 20 10 10 30 50 0 20 10 20 40 0 0 10 20

Foxtail, Giant 0 0 0 30 90 0 50 60 30 100 0 0 60 10

Galium 30 30 30 70 70 0 80 20 70 100 0 0 40 20

Kochia 30 30 30 100 100 0 90 50 60 100 0 0 0 0

Pigweed 30 30 30 40 60 0 90 50 100 100 0 0 20 10

Ragweed 0 0 0 0 0 0 10 0 0 20 0 0 0 0

Ryegrass, Italian 0 0 0 20 30 0 30 0 0 50 0 0 0 0

Wheat 0 0 0 40 30 0 20 0 20 20 0 0 0 0

Table A Compounds

125 g ai/ha 97 98 99 100 101 102 103 104 105 106 107 108 109 110

Postemergence

Barnyardgrass 20 10 80 50 20 0 30 0 0 40 90 10 0 60 Blackgrass 20 10 80 40 0 0 10 20 10 0 90 0 0 50

Corn 10 10 50 10 0 0 20 10 0 0 60 20 20 50

Foxtail, Giant 60 20 90 70 20 0 70 10 0 10 90 10 0 90

Galium 100 50 70 70 40 0 100 30 20 0 90 40 30 100

Kochia 40 0 40 80 20 0 100 10 10 - 90 40 20 100

Pigweed 50 90 40 70 60 0 100 40 30 10 100 50 60 100

Ragweed 20 10 30 0 0 0 0 0 0 0 30 0 20 0

Ryegrass, Italian 30 0 50 20 10 0 0 0 0 0 80 0 0 20

Wheat 0 10 30 0 0 0 0 0 0 0 30 0 0 20

Table A Compounds

125 g ai/ha 111 112 113 114 115 116 117 118 119 120 121 122 123 124

Postemergence

Barnyardgrass 0 10 40 10 0 10 10 10 0 0 40 50 50 60

Blackgrass 0 30 40 10 20 0 10 0 0 0 30 60 50 60

Corn 0 0 20 20 10 10 10 10 20 0 10 20 10 20

Foxtail, Giant 0 30 50 20 0 20 10 10 0 0 70 40 50 70

Galium 0 80 80 80 20 60 100 30 90 30 80 60 100 90

Kochia 0 30 100 80 0 10 50 60 30 0 80 80 90 80

Pigweed 0 70 100 100 40 50 70 60 100 20 100 100 100 100

Ragweed 0 40 20 20 0 0 20 10 10 0 50 10 10 20

Ryegrass, Italian 0 0 30 10 0 0 0 0 0 0 20 20 20 20

Wheat 0 0 20 10 0 0 0 0 0 0 10 0 0 10

Table A Compounds

125 g ai/ha 125 126 127 128 129 130 131 132 133 134 135 136 137 138

Postemergence

Barnyardgrass 30 0 30 20 100 90 10 50 30 20 10 30 60 90

Blackgrass 30 0 20 20 80 50 0 30 0 20 20 50 30 90

Corn 10 0 20 10 20 20 30 30 20 10 20 20 10 60

Foxtail, Giant 50 0 50 20 100 40 20 50 30 20 20 30 60 90

Galium 100 0 90 80 90 100 50 60 50 40 80 40 100 100

Kochia 100 0 60 60 100 100 90 70 20 60 60 80 100 100

Pigweed 100 10 30 50 70 100 80 90 50 80 90 100 100 100

Ragweed 30 0 0 0 0 30 0 0 0 10 10 20 40 60

Ryegrass, Italian 20 0 0 0 60 20 20 0 0 10 10 10 30 100

Wheat 20 0 10 10 10 30 20 20 0 10 0 10 10 40

Table A Compounds

125 g ai/ha 139 140 141 142 143 144 145 146 Postemergence

Barnyardgrass 0 0 20 0 70 90 80 90

Blackgrass 0 0 10 0 80 90 60 90

Corn 0 0 20 10 30 80 50 80

Foxtail, Giant 0 0 40 0 70 90 70 90

Galium 0 0 60 20 100 100 80 100

Kochia 0 30 60 10 100 100 90 100

Pigweed 0 20 70 20 100 100 100 70

Ragweed 0 0 20 20 50 10 20 30

Ryegrass, Italian 0 0 10 0 80 80 40 70

Wheat 0 0 0 0 20 60 30 20

Table A Compounds

31 g ai/ha 1 2 3 4 5 19 36 37 38 43 44 45 46 50

Postemergence

Barnyardgrass 20 30 20 0 0 0 0 0 10 0 0 20 0 0

Blackgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Corn 0 10 0 0 0 0 0 0 0 0 0 0 0 10

Foxtail, Giant 30 30 30 0 0 0 0 0 40 0 0 20 0 20

Galium 50 60 40 0 0 0 0 10 50 20 0 50 50 60

Kochia 20 50 0 0 0 0 0 0 30 0 0 20 30 60

Pigweed 40 60 70 0 0 10 0 20 80 10 0 80 60 80

Ragweed 0 0 0 0 0 0 0 0 0 0 0 10 0 0

Ryegrass, Italian 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Table A Compounds

31 g ai/ha 51 53 54 62 63 66 67 68 69 70 71 74 76 77

Postemergence

Barnyardgrass 0 0 0 20 0 40 0 10 10 0 0 10 0 30

Blackgrass 0 0 0 0 0 10 0 10 10 0 10 10 0 20

Corn 0 0 0 0 10 20 0 10 0 10 10 10 0 10

Foxtail, Giant 0 0 0 0 0 30 0 20 20 0 10 20 0 30

Galium 0 0 0 30 0 30 0 20 40 30 30 20 0 90

Kochia 0 0 0 60 20 20 0 20 20 20 10 20 0 100

Pigweed 0 0 0 50 20 40 0 20 40 10 30 60 0 100

Ragweed 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Ryegrass, Italian 0 0 0 0 0 0 0 0 0 0 0 0 0 20

Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Table A Compounds

31 g ai/ha 80 81 82 86 87 88 89 90 92 93 94 95 96 97

Postemergence

Barnyardgrass 30 10 30 20 40 0 30 0 40 0 0 0 0 10

Blackgrass 30 10 40 0 10 0 20 0 10 0 0 0 0 0

Corn 10 10 20 30 40 0 10 0 10 0 0 0 0 10

Foxtail, Giant 30 20 30 10 40 0 20 10 50 0 0 0 0 10

Galium 60 30 90 30 30 0 30 0 90 0 0 10 0 100

Kochia 50 30 80 90 100 0 80 30 100 0 0 0 0 -

Pigweed 80 50 100 30 40 0 90 10 100 0 0 10 0 20

Ragweed 10 0 40 0 0 0 10 0 0 0 0 0 0 10

Ryegrass, Italian 0 0 40 0 0 0 10 0 0 0 0 0 0 20

Wheat 0 0 10 30 20 0 0 0 0 0 0 0 0 0

Table A Compounds

31 g ai/ha 98 99 100 101 102 103 104 105 107 108 109 110 111 112

Postemergence

Barnyardgrass 0 30 10 10 0 0 0 0 40 0 0 30 0 0

Blackgrass 0 30 0 0 0 0 0 0 50 0 0 0 0 0

Corn 0 0 10 0 0 20 0 0 30 10 10 20 0 0

Foxtail, Giant 0 50 20 0 0 10 0 0 70 0 0 30 0 0

Galium 10 20 20 10 0 70 10 10 90 20 0 70 0 60

Kochia 0 20 60 0 0 70 0 0 90 20 0 100 0 0

Pigweed 30 10 30 20 0 90 10 10 100 20 20 90 0 40

Ragweed 0 10 0 0 0 0 0 0 20 0 0 0 0 20

Ryegrass, Italian 0 0 0 0 0 0 0 0 20 0 0 0 0 0

Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Table A Compounds

31 g ai/ha 113 114 115 116 117 118 119 120 121 122 123 124 126 127

Postemergence

Barnyardgrass 10 0 0 0 0 0 0 0 20 10 10 10 0 10

Blackgrass 0 0 0 0 0 0 0 0 20 20 10 20 0 10

Corn 10 10 0 0 10 0 10 0 10 10 10 10 0 10

Foxtail, Giant 10 0 0 0 0 0 0 0 10 10 20 30 0 10

Galium 40 50 20 30 60 10 10 0 70 30 90 70 0 60

Kochia 80 20 0 0 20 30 30 0 20 80 50 50 0 10

Pigweed 90 50 10 40 30 40 70 0 80 70 70 70 0 20

Ragweed 0 0 0 0 0 0 0 0 20 0 0 10 0 0 Ryegrass, Italian 0 0 0 0 0 0 0 0 10 0 0 0 0 0

Wheat 0 0 0 0 0 0 0 0 10 0 0 10 0 0

Table A Compounds

31 g ai/ha 128 129 131 132 133 134 135 137 138 140 141 142 143 144

Postemergence

Barnyardgrass 0 20 0 30 10 0 0 20 90 0 10 0 20 40

Blackgrass 0 20 0 0 0 10 0 10 40 0 0 0 30 50

Corn 10 20 20 20 0 10 10 10 30 0 10 0 10 20

Foxtail, Giant 10 20 0 30 10 10 10 10 90 0 20 0 30 60

Galium 20 30 20 20 30 10 50 40 70 0 40 0 90 40

Kochia 10 40 40 40 0 20 10 90 90 0 50 0 90 90

Pigweed 20 20 50 60 30 40 40 80 100 0 40 0 100 90

Ragweed 0 0 0 0 0 0 0 10 30 0 0 0 20 10

Ryegrass, Italian 0 0 0 0 0 0 0 10 30 0 0 0 20 30

Wheat 0 0 0 0 0 0 0 0 20 0 0 0 10 10

Table A Compounds Table A Compounds

31 g ai/ha 145 146 1000 g ai/ha 12 55 56 57 5 8 59

Postemergence Preemergence

Barnyardgrass 30 30 Barnyardgrass ε 10 0 90 50 90 20

Blackgrass 40 30 Corn - 0 0 0 20 0

Corn 30 20 Crabgrass, Large - 0 100 100 100 80

Foxtail, Giant 50 30 Foxtail, Giant 100 0 100 90 100 30

Galium 40 70 Kochia 0 - - -

Kochia 70 70 Morningglory - - 0 0 0

Pigweed 90 60 Pigweed 100 0 100 60 50 30

Ragweed 10 0 Ragweed ε !O - - -

Ryegrass, Italian 10 0 Ryegrass, Italian 40 - - -

Wheat 10 20 Velvetleaf - 0 90 20 20 0

Wheat - 0 0 0 20 0

Table A Compounds

500 g ai/ha 6 7 8 9 10 11 13 14 15 16 17 18 20 21

Preemergence

Barnyardgrass 60 100 100 90 100 30 100 60 100 100 0 0 100 100

Corn

Crabgrass, Large

Foxtail, Giant 100 100 100 100 100 100 100 100 100 100 0 0 100 100

Kochia 0 100 0 100 100 0 100 70 100 80 0 10 100 100 wormnggiory

Pigweed 70 100 60 100 100 20 100 100 100 100 10 40 100 100

Ragweed 0 50 0 0 0 0 0 10 10 0 0 0 0 0

Ryegrass, Italian 70 30 30 30 30 0 90 20 90 20 0 0 90 90

Velvetleaf

Wheat

Table A Compounds

500 g ai/ha 22 23 24 25 26 27 28 30 31 32 33 34 35 39

Preemergence

Barnyardgrass 100 70 30 30 100 0 20 0 0 0 100 90 90 0

Corn - - - - - 0 0 - - - - - - -

Crabgrass, Large - - - - - 0 50 - - - - - - -

Foxtail, Giant 100 100 20 60 100 0 20 100 0 0 100 100 100 0

Kochia 100 50 0 50 100 - - 100 0 0 100 40 80 0

Morningglory - - - - - 0 0 - - - - - - -

Pigweed 100 100 90 80 100 0 80 100 0 30 100 100 100 0

Ragweed 0 10 0 0 20 - - 0 0 0 20 0 0 0

Ryegrass, Italian 90 40 0 0 100 - - 0 0 0 100 0 30 0

Velvetleaf - - - - - 0 20 - - - - - - -

Wheat - - - - - 0 0 - - - - - - -

Table A Compounds

500 g ai/ha 40 41 42 47 48 49 61 64 65 72 73 75 78 79

Preemergence

Barnyardgrass 50 0 0 0 10 0 100 0 100 100 100 100 100 100

Corn

Crabgrass, Large

Foxtail, Giant 100 0 0 0 10 0 100 0 100 100 100 100 100 100

Kochia 90 30 0 0 0 0 100 0 90 100 100 100 60 100

Morningglory

Pigweed 100 40 30 0 0 0 100 0 100 100 100 100 100 100

Ragweed 0 80 0 0 0 0 20 0 80 10 50 10 0 90

Ryegrass, Italian 0 0 0 0 0 0 80 0 30 30 90 100 20 100

Velvetleaf

Wheat

Table A Compounds

500 g ai/ha 83 84 85 91 106 125 130 136 139

Preemergence Barnyardgrass 100 100 100 100 100

Corn

Crabgrass, Large

Foxtail, Giant 100 100 70 100 100 100 100 100

Kochia 0 0 0 100 90 100 100 100

Morningglory

Pigweed 90 100 60 100 70 100 100 100

Ragweed 0 0 0 0 0 40 90 80

Ryegrass, Italian 0 0 0 80 10 100 100 100

Velvetleaf

Wheat

Table A Compounds

125 g ai/ha 1 2 3 4 5 6 7 8 9 10 11 13 15 16

Preemergence

Barnyardgrass 30 50 80 0 0 10 50 30 40 40 0 100 100 30

Foxtail, Giant 70 100 100 0 0 60 90 100 100 100 40 100 100 90

Kochia 40 70 40 0 0 0 50 0 70 90 0 90 100 90

Pigweed 70 90 100 0 0 10 100 10 100 100 0 100 100 90

Ragweed 0 0 0 0 0 0 - 0 0 0 0 0 0 0

Ryegrass, Italian 0 10 30 0 0 0 0 0 10 10 0 10 40 0

Table A Compounds

125 g ai/ha 17 18 19 20 21 22 23 24 25 26 30 31 32 33

Preemergence

Barnyardgrass 0 0 0 100 100 40 20 0 0 100 0 0 0 100

Foxtail, Giant 0 0 0 100 100 100 70 0 10 100 100 0 0 100

Kochia 0 0 20 30 40 30 0 0 0 100 90 0 0 60

Pigweed 0 10 20 100 100 100 100 0 40 100 100 0 30 100

Ragweed 0 0 0 0 0 0 0 0 0 20 0 0 0 0

Ryegrass, Italian 0 0 0 30 30 30 0 0 0 70 0 0 0 40

Table A Compounds

125 g ai/ha 34 35 36 37 38 39 40 41 42 43 44 45 46 47

Preemergence

Barnyardgrass 0 70 0 30 90 0 0 0 0 40 0 0 20 0

Foxtail, Giant 70 100 0 70 100 0 20 0 0 60 40 10 100 0

Kochia 20 30 0 0 40 0 60 30 0 100 0 0 70 0

Pigweed 40 100 0 0 100 0 40 30 0 90 0 70 100 0

Ragweed 0 0 0 0 0 0 0 50 0 0 0 0 0 0 Ryegrass, Italian 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Table A Compounds

125 g ai/ha 48 49 50 51 53 54 61 62 63 64 65 66 67 68

Preemergence

Barnyardgrass 0 0 10 0 0 0 50 70 100 0 30 100 0 70

Foxtail, Giant 0 0 100 0 0 0 100 100 90 0 100 100 0 80

Kochia 0 0 0 0 0 0 90 70 0 0 60 40 0 30

Pigweed 0 0 90 0 0 0 100 90 90 0 100 100 0 80

Ragweed 0 0 0 0 0 0 0 0 0 0 0 100 0 0

Ryegrass, Italian 0 0 0 0 0 0 30 10 0 0 10 30 0 0

Table A Compounds

125 g ai/ha 69 70 71 72 73 74 75 76 77 78 79 80 81 82

Preemergence

Barnyardgrass 90 20 10 90 100 60 100 70 100 60 100 100 90 100

Foxtail, Giant 70 60 100 90 100 100 100 70 100 90 100 100 100 100

Kochia 30 0 0 90 100 100 80 0 100 20 80 100 90 80

Pigweed 100 0 40 100 100 90 100 50 100 80 100 100 100 100

Ragweed 0 0 0 0 10 0 0 0 0 0 30 20 0 60

Ryegrass, Italian 0 0 0 10 50 20 80 0 70 0 90 50 20 80

Table A Compounds

125 g ai/ha 83 84 85 86 87 88 89 90 91 92 93 94 95 96

Preemergence

Barnyardgrass 30 0 0 90 100 0 90 40 90 100 0 0 70 0

Foxtail, Giant 90 0 0 50 100 0 50 70 70 100 0 0 50 0

Kochia 0 0 0 100 90 0 50 0 20 90 0 0 0 0

Pigweed 30 0 0 100 100 0 100 0 40 100 0 0 40 0

Ragweed 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Ryegrass, Italian 0 0 0 20 20 0 20 0 0 80 0 0 0 0

Table A Compounds

125 g ai/ha 97 98 99 100 101 102 103 104 105 106 107 108 109 110

Preemergence

Barnyardgrass 10 30 100 100 10 0 50 30 30 0 100 30 20 100

Foxtail, Giant 70 40 100 100 40 0 60 40 20 80 100 80 40 100

Kochia 0 0 80 0 0 0 70 0 0 30 100 10 0 100

Pigweed 20 0 90 60 0 0 100 40 20 30 100 70 60 100

Ragweed 0 0 10 0 0 0 0 0 0 0 20 0 0 0 Ryegrass, Italian 0 0 30 0 0 0 0 0 0 0 80 0 0 70

Table A Compounds

125 g ai/ha 111 112 113 114 115 116 117 118 119 120 121 122 123 124

Preemergence

Barnyardgrass 0 80 90 20 0 0 0 0 20 0 30 90 70 80

Foxtail, Giant 0 70 100 90 0 30 20 20 90 0 100 40 100 100

Kochia 0 50 60 10 0 0 0 0 0 0 0 70 10 10

Pigweed 0 100 100 30 0 70 30 50 100 0 0 90 80 100

Ragweed 0 0 0 80 0 0 0 50 0 0 0 0 0 0

Ryegrass, Italian 0 0 40 0 0 0 0 0 0 0 0 30 20 20

Table A Compounds

125 g ai/ha 125 126 127 128 129 130 131 132 133 134 135 136 137 138

Preemergence

Barnyardgrass 100 0 60 50 100 100 100 100 30 80 40 100 90 100

Foxtail, Giant 100 0 100 100 100 100 90 100 90 90 50 100 100 100

Kochia 100 0 30 0 100 100 100 60 10 10 0 100 70 100

Pigweed 100 0 70 30 100 100 100 100 100 50 20 100 100 100

Ragweed 20 0 0 0 0 20 0 0 0 0 0 80 0 0

Ryegrass, Italian 70 0 10 10 60 80 20 30 0 20 10 20 20 100

Table A Compounds Table A Compounds

125 g ai/ha 139 140 141 142 143 144 145 146 31 g ai/ha 145 146

Preemergence Preemergence

Barnyardgrass 0 0 60 0 100 100 80 100 Barnyardgrass 40 20

Foxtail, Giant 0 0 100 0 100 100 100 100 Foxtail , Giant 90 80

Kochia 0 40 20 0 100 100 40 80 Kochia 0 60

Pigweed 0 10 90 0 - 100 100 100 Pigweed 100 60

Ragweed 50 0 30 0 0 10 30 0 Ragweed 0 0

Ryegrass, Italian 0 10 10 0 70 70 50 50 Ryegrass , Italian 10 0

Table A Compounds

31 g ai/ha 1 2 3 4 5 19 36 37 38 43 44 45 46 50

Preemergence

Barnyardgrass 20 10 60 0 0 0 0 0 20 0 0 0 0 0

Foxtail, Giant 30 70 70 0 0 0 0 20 30 0 0 0 40 50

Kochia 0 30 0 0 0 0 0 0 0 100 0 0 0 0

Pigweed 20 40 50 0 0 0 0 0 60 30 0 0 50 0

Ragweed 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Ryegrass, Italian 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Table A Compounds

31 g ai/ha 51 53 54 62 63 66 67 68 69 70 71 74 76 77

Preemergence

Barnyardgrass 0 0 0 30 40 90 0 10 70 0 0 10 0 20

Foxtail, Giant 0 0 0 30 10 70 0 10 40 0 40 40 0 100

Kochia 0 0 0 20 0 0 0 0 0 0 0 0 0 80

Pigweed 0 0 0 60 0 20 0 20 40 0 0 20 0 100

Ragweed 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Ryegrass, Italian 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Table A Compounds

31 g ai/ha 80 81 82 86 87 88 89 90 92 93 94 95 96 97

Preemergence

Barnyardgrass 60 10 50 0 70 0 20 0 70 0 0 10 0 0

Foxtail, Giant 90 30 90 0 60 0 10 10 100 0 0 0 0 40

Kochia 100 0 70 10 30 0 10 0 90 0 0 0 0 0

Pigweed 100 100 90 20 40 0 10 0 100 0 0 0 0 0

Ragweed 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Ryegrass, Italian 0 0 0 0 0 0 0 0 30 0 0 0 0 0

Table A Compounds

31 g ai/ha 98 99 100 101 102 103 104 105 107 108 109 110 111 112

Preemergence

Barnyardgrass 0 70 40 0 0 0 0 0 90 10 0 40 0 0

Foxtail, Giant 0 90 50 0 0 10 0 0 100 10 0 80 0 0

Kochia 0 40 0 0 0 0 0 0 90 0 0 10 0 0

Pigweed 0 50 0 0 0 40 0 0 100 0 0 40 0 60

Ragweed 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Ryegrass, Italian 0 0 0 0 0 0 0 0 30 0 0 0 0 10

Table A Compounds

31 g ai/ha 113 114 115 116 117 118 119 120 121 122 123 124 126 127

Preemergence

Barnyardgrass 0 0 0 0 0 0 0 0 0 30 20 10 0 20

Foxtail, Giant 60 10 0 0 0 0 50 0 30 0 40 60 0 30

Kochia 10 0 70 0 0 0 0 0 20 10 0 0 0 0

Pigweed 100 0 0 50 0 20 20 0 0 40 0 40 0 0

Ragweed 0 20 20 30 0 100 0 0 0 0 0 0 0 0 Ryegrass, Italian 10 0 0 0 0 0 0 0 10 0 0 0 0 0

Table A Compounds

31 g ai/ha 128 129 131 132 133 134 135 137 138 140 141 142 143 144

Preemergence

Barnyardgrass 20 70 0 30 0 0 0 0 70 0 0 0 20 80

Foxtail, Giant 30 100 0 40 0 10 0 70 90 0 10 0 100 100

Kochia 0 30 10 10 0 0 0 0 50 0 10 0 100 90

Pigweed 0 90 90 70 70 0 0 10 80 0 0 0 - 100

Ragweed 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Ryegrass, Italian 0 20 0 0 0 0 0 0 10 10 0 0 20 20

TEST B

Plant species in the flooded paddy test selected from rice (Oryza sativa), sedge, umbrella (small-flower umbrella sedge, Cyperus difformis), ducksalad (Heteranthera limosd), and barnyardgrass (Echinochloa crus-galli) were grown to the 2-leaf stage for testing. At time of treatment, test pots were flooded to 3 cm above the soil surface, treated by application of test compounds directly to the paddy water, and then maintained at that water depth for the duration of the test. Treated plants and controls were maintained in a greenhouse for 13 to 15 days, after which time all species were compared to controls and visually evaluated. 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 Compounds

250 g ai/ha 1 2 3 4 5 6 7 8 9 10 11 12 13 18

Flood

Barnyardgrass 0 0 0 0 0 0 0 0 20 0 0 0 0 0

Ducksalad 20 30 30 0 0 0 0 0 75 80 0 0 70 0

Rice 0 0 0 0 0 0 0 0 0 0 0 0 30 0

Sedge, Umbrella 80 100 100 0 0 0 0 70 75 80 0 0 75 0

Table B Compounds

250 g ai/ha 19 20 21 22 23 24 25 26 30 33 35 36 37 38 Flood

Barnyardgrass 0 0 30 0 0 0 0 60 0 0 0 0 0 0

Ducksalad 0 30 70 40 30 0 0 100 40 80 50 0 0 40

Rice 0 0 0 0 15 0 0 20 0 0 0 0 0 0

Sedge, Umbrella 0 40 100 50 95 0 0 100 0 95 60 0 0 30

Table B Compounds

250 g ai/ha 43 44 45 46 47 48 49 50 51 53 54 56 57 58 Flood

Barnyardgrass 0 0 0 0 0 20 20 0 15 0 0 0 0 0

Ducksalad 0 0 0 75 0 0 0 65 0 0 0 0 0 0

Rice 0 0 0 10 0 20 20 0 15 0 0 0 0 0

Sedge, Umbrella 0 30 0 80 0 0 0 80 0 0 0 0 0 0

Table B Compounds

250 g ai/ha 61 62 63 64 65 66 67 68 69 70 71 74 75 76

Flood

Barnyardgrass 20 40 45 0 0 30 0 0 0 0 0 40 40 0

Ducksalad 100 100 100 0 70 100 0 0 75 70 90 100 95 85

Rice 0 0 25 0 0 0 0 0 20 0 0 0 35 10

Sedge, Umbrella 100 90 100 0 85 95 0 0 80 80 95 100 95 70

Table B Compounds

250 g ai/ha 77 78 79 80 81 82 83 84 85 86 87 88 89 90

Flood

Barnyardgrass 15 20 60 75 45 35 0 0 0 40 50 0 40 0

Ducksalad 85 70 90 100 100 100 80 0 0 100 100 0 95 30

Rice 0 15 45 55 0 30 0 0 0 20 35 20 40 0

Sedge, Umbrella 100 80 100 100 100 95 80 0 0 100 100 0 95 60

Table B Compounds

250 g ai/ha 91 92 93 94 95 96 97 98 99 100 101 102 103 104

Flood

Barnyardgrass 0 25 0 0 0 0 0 0 60 40 0 0 0 0

Ducksalad 100 100 0 0 30 0 70 0 100 90 0 80 95 75

Rice 20 0 0 0 0 0 0 0 40 0 0 0 20 0

Sedge, Umbrella 95 100 0 0 0 0 75 0 90 70 0 80 95 75

Table B Compounds

250 g ai/ha 105 106 107 108 109 110 111 112 113 114 115 116 117 118

Flood

Barnyardgrass 0 0 50 0 0 25 0 20 65 0 0 30 0 0

Ducksalad 40 0 95 80 0 75 0 100 80 40 0 75 20 0

Rice 0 0 35 0 0 25 0 40 20 0 0 70 0 0

Sedge, Umbrella 0 0 95 60 0 90 0 100 90 90 0 90 60 50

Table B Compounds

250 g ai/ha 119 120 121 122 123 124 125 126 127 128 129 130 131 132

Flood Barnyardgrass 0 0 50 80 40 45 45 90 40 20 45 55 15 45

Ducksalad 100 0 0 100 95 100 70 0 90 90 90 40 80 90

Rice 0 0 35 40 35 40 35 0 15 15 40 35 15 45

Sedge, Umbrella 90 0 70 100 95 100 90 0 90 85 80 98 90 80

Table B Compounds

250 g ai/ha 133 134 135 136 137 138 139 1 40 141 142 143 144 145 146

Flood

Barnyardgrass 0 0 0 45 75 50 0 0 20 0 50 70 50 40

Ducksalad 0 95 85 60 95 100 30 0 70 0 90 100 100 100

Rice 30 20 20 35 50 45 0 0 10 0 40 35 30 35

Sedge, Umbrella 0 95 85 80 95 85 0 0 50 0 90 100 100 85

TEST C

Seeds of plant species selected from blackgrass (Alopecurus myosuroides), ryegrass, Italian (Italian ryegrass, Lolium multiflorum), wheat (winter wheat, Triticum aestivum), galium (catchweed bedstraw, Galium aparine), corn (Zea mays), crabgrass, large (large crabgrass, Digitaria sanguinalis), foxtail, giant (giant foxtail, Setaria faberii), johnsongrass (Sorghum halepense), lambsquarters (Chenopodium album), morningglory (Ipomoea coccinea), nutsedge, yellow (yellow nutsedge, Cyperus esculentus), pigweed (Amaranthus retroflexus), ragweed (common ragweed, Ambrosia elatior), soybean (Glycine max), barnyardgrass (Echinochloa crus-galli), oilseed rape (Brassica napus), pigweed, palmer (palmer pigweed, Amaranthus palmeri), waterhemp (common waterhemp, Amaranthus rudis), velvetleaf (Abutilon theophrasti), kochia (Kochia scoparia), Surinam grass (Brachiaria decumbens), nightshade (eastern black nightshade, Solanum ptycanthum), wild poinsettia (Euphorbia heterophylla), windgrass (Apera spica-venti), and oat, wild (wild oat Avena fatua), were planted into a blend of loam soil and sand or a silt loam soil and treated preemergence with test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant.

At the same time, plants selected from these crop and weed species and also chickweed (common chickweed, Stellaria media), buckwheat, wild (wild buckwheat, Polygonum convolvulus), wild mustard (Sinapis arvensis), field poppy (Papaver rhoeas), field violet (Viola arvensis), geranium, cutleaf (cutleaf geranium, Geranium dissectum), Canada thistle (Cirsium arvense), and speedwell (bird's-eye speedwell, Veronica persica), were planted in pots containing Sunshine Redi-Earth ^® planting medium comprising spaghnum peat moss, vermiculite, starter nutrients and dolomitic limestone and treated with postemergence applications of test chemicals formulated in the same manner. Plants ranged in height from 2 to 18 cm (1- to 4-leaf stage) for postemergence treatments. Treated plants and controls were maintained in a greenhouse for 13 to 15 d, after which time all species were compared to controls and visually evaluated. 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.

Plant species in the flooded paddy test consisted of rice (Oryza sativa), sedge, umbrella (small-flower umbrella sedge Cyperus difformis), ducksalad (Heter anther a limosd), and barnyardgrass (Echinochloa crus-galli) grown to the 2-leaf stage for testing. At time of treatment, test pots were flooded to 3 cm above the soil surface, treated by application of test compounds directly to the paddy water, and then maintained at that water depth for the duration of the test.

Table C Compounds

125 g ai/ha 7 15 16 20 21 22 23 26 33 35 72 73 75 77 Postemergence

Barnyardgrass 10 20 20 20 20 10 20 30 25 15 10 30 - 30

Blackgrass 5 10 5 10 5 5 20 35 20 10 30 35 30 25

Buckwheat, Wild _ _ _ _ _ _ _ _ _ _ _ _ g5 _

Canada Thistle _ _ _ _ _ _ _ _ _ _ _ _ ₁₀ o

Chickweed 50 90 80 75 80 60 85 98 85 50 98 85 98 100

Corn 15 20 20 20 20 15 10 25 30 20 20 15 20 25

Crabgrass, Large 15 25 25 15 35 25 25 65 15 10 50 60 25 30

Field Poppy _ _ _ _ _ _ _ _ _ _ _ _ ₁₀ o

Field Violet _ _ _ _ _ _ _ _ _ _ _ _ ₁₀ o

Foxtail, Giant 15 35 35 25 15 25 30 25 20 20 20 25 25 70

Galium 40 95 55 98 80 70 80 95 85 60 98 98 80 98

Geranium, Cutleaf _ _ _ _ _ _ _ _ _ _ _ _ 55 _

Johnsongrass - - - - - - 20 25 20 10 10 20 70

Kochia 20 95 90 100 90 50 85 95 95 90 100 100 98 100

Lambsquarters 55 95 60 85 85 75 80 98 90 70 85 98 90 90

Morningglory 55 90 75 70 70 50 35 85 65 60 70 75 65 80

Mustard, Wild _ _ _ _ _ _ _ _ _ _ _ _ _ _

Nightshade _ _ _ _ _ _ _ _ _ _ _ _ ₉₈ _

Nutsedge, Yellow 5 20 20 10 10 5 10 10 10 5 15 30 5 15

Oat, Wild 5 10 10 5 5 5 5 35 30 0 10 10 35 15

Oilseed Rape 5 0 70 60 30 80 35 80 95 65 65 50 95 85

Pigweed 70 98 50 95 90 95 85 100 100 98 100 100 - 100

Pigweed, Palmer _ _ _ _ _ _ _ _ _ _ _ _ 35 -

Poinsettia, Wild _ _ _ _ _ _ _ _ _ _ _ _ go -

Ragweed 25 65 40 60 55 50 50 90 60 20 75 65 60 70 Ryegrass, Italian 30 5 5 5 15 5 5 10 30 5 15 20 5 10

Soybean 70 90 50 60 60 75 35 75 55 35 70 60 85 65

Speedwell 100 -

Surinam Grass 20 -

Velvetleaf 40 85 50 70 70 85 40 80 75 40 70 75 75 65

Waterhemp 65 - - 98 85 80 95 100 100 95 90 100 95 100

Wheat 5 0 0 5 0 0 0 10 5 0 5 5 10 30

Windgrass 5 -

Table C Compounds

125 g ai/ha 79 80 82 89 92 107 110 125 130 136 137 138 143 144

Postemergence

Barnyardgrass - - 60 - 20 - 30 10 20 10 40 - 20 10

Blackgrass 30 25 45 45 20 60 25 30 30 15 40 65 40 15

Buckwheat, Wild 90 95 100 85 - 100 80 98 80 80 90 100 100 95

Canada Thistle 100 85 98 85 - 90 95 90 98 85 100 95 100 90

Chickweed 98 90 90 100 100 100 90 98 90 80 100 100 100 85

Corn 20 25 25 20 20 30 15 20 20 20 25 30 30 25

Crabgrass, Large 65 30 20 90 35 60 60 20 20 30 70 95 30 25

Field Poppy 100 85 100 100 - 100 100 100 100 90 100 100 100 100

Field Violet 90 95 90 100 - 100 100 98 100 100 85 100 100 90

Foxtail, Giant 40 15 20 20 50 25 25 25 30 25 35 65 25 40

Galium 95 90 90 90 100 95 90 90 80 75 85 85 95 90

Geranium, Cutleaf 65 60 60 55 - 75 60 55 60 45 35 60 75 40

Johnsongrass 85 5 30 85 - 98 15 25 15 15 25 90 20 5

Kochia 98 80 95 95 100 98 100 98 98 90 98 98 100 90

Lambsquarters 100 85 90 100 85 100 98 100 95 80 90 100 95 85

Morningglory 30 60 75 55 85 95 50 75 55 35 20 65 65 60

Mustard, Wild - 90 100 - - 100 100 100 100 100 100 100 100 95

Nightshade 100 75 100 95 - 100 98 90 90 80 90 98 90 90

Nutsedge, Yellow 5 5 10 5 20 5 5 10 5 5 5 30 25 10

Oat, Wild 35 5 50 30 5 45 55 15 15 10 10 70 20 35

Oilseed Rape 100 70 95 100 70 98 95 95 98 80 100 100 100 85

Pigweed - - - - 100 - - - - - - - - -

Pigweed, Palmer 85 60 98 85 - 100 95 85 65 70 70 98 100 80

Poinsettia, Wild 85 75 75 90 - 90 90 85 75 75 75 90 75 60

Ragweed 65 35 55 25 70 45 60 55 50 35 30 75 55 15

Ryegrass, Italian 30 5 25 10 30 50 20 15 15 10 10 35 20 20 Soybean 65 95 40 70 75 95 35 70 95 40 40 55 65 65

Speedwell 100 100 95 100 - 100 95 98 98 85 100 100 100 95

Surinam Grass 35 25 25 20 - 35 25 20 20 10 20 35 20 25

Velvetleaf 90 55 75 70 85 90 75 30 75 70 70 75 70 65

Waterhemp 98 90 95 95 100 100 95 90 85 75 75 100 90 75

Wheat 15 15 30 15 10 30 15 25 30 5 20 35 30 15

Windgrass 30 30 35 35 - 50 30 35 35 30 45 50 40 30

Table C Compounds

62 g ai/ha 7 15 16 20 21 22 23 26 33 35 72 73 75 77

Postemergence

Barnyardgrass 15 20 20 10 20 10 10 20 10 10 10 20 - 25

Blackgrass 0 10 0 5 5 0 15 15 10 10 10 40 10 20

Buckwheat, Wild 80 -

Canada Thistle 75 -

Chickweed 30 90 50 65 50 65 50 85 85 45 90 90 90 100

Corn 10 20 15 10 15 5 5 20 25 20 10 15 15 20

Crabgrass, Large 20 25 25 15 25 25 20 25 10 15 10 25 15 30

Field Poppy 80 -

Field Violet 98 -

Foxtail, Giant 10 20 30 10 20 15 25 10 10 10 20 20 10 25

Galium 10 95 55 80 75 60 55 95 80 55 5 75 70 95

Geranium, Cutleaf 35 -

Johnsongrass - - - - - - 15 20 20 10 10 20 10 -

Kochia 25 95 80 100 90 85 55 90 95 60 100 100 90 100

Lambsquarters 30 75 40 70 65 70 65 98 80 65 75 90 70 70

Morningglory 40 85 40 70 40 35 60 65 75 60 40 85 20 90

Mustard, Wild

Nightshade 85 -

Nutsedge, Yellow 5 5 10 5 5 5 5 10 5 0 10 20 0 15

Oat, Wild 5 5 5 5 5 0 10 15 25 0 5 5 40 10

Oilseed Rape 0 100 60 50 50 55 50 75 55 50 0 98 80 70

Pigweed 60 95 85 98 90 70 70 98 98 90 85 100 - 100

Pigweed, Palmer 95 -

Poinsettia, Wild 80 -

Ragweed 20 50 10 55 45 50 40 55 50 10 40 60 50 35

Ryegrass, Italian 30 10 0 10 0 0 5 10 5 5 10 10 10 10

Soybean 40 80 50 55 60 35 70 65 30 35 40 75 85 70 Speedwell - 100

Surinam Grass - 20

Velvetleaf 35 60 30 40 60 55 35 75 65 35 40 70 70 55

Waterhemp 60 90 90 85 35 98 100 90 90 100 90 100

Wheat 5 5 0 0 0 5 0 0 0 5 0 10

Windgrass 10

Table C Compounds

62 g ai/ha 79 80 82 89 92 107 110 125 130 136 137 138 143 144

Postemergence

Barnyardgrass - - 10 - 15 - 20 5 10 10 20 - 10 10

Blackgrass 20 5 40 30 5 20 20 15 20 10 15 10 15 15

Buckwheat, Wild 85 75 100 75 - 75 95 75 75 90 98 100 100 80

Canada Thistle 70 75 85 85 - 90 98 90 98 85 98 90 90 90

Chickweed 95 75 90 85 100 98 95 90 80 75 90 100 85 85

Corn 20 15 25 15 15 20 20 15 15 20 15 25 20 20

Crabgrass, Large 70 10 30 85 25 30 25 15 10 10 40 85 15 20

Field Poppy 100 85 100 100 - 98 100 100 100 80 100 100 90 90

Field Violet 85 90 90 100 - 98 95 98 95 95 85 100 98 80

Foxtail, Giant 25 10 10 10 25 20 25 10 10 10 40 30 10 30

Galium 85 85 85 80 100 90 75 80 85 60 75 80 80 85

Geranium, Cutleaf 55 35 40 50 - 60 40 55 45 50 30 55 60 35

Johnsongrass 60 5 10 10 - 35 10 10 10 10 10 80 10 5

Kochia 90 80 95 80 100 95 100 95 95 85 98 95 100 90

Lambsquarters 90 80 85 100 50 100 95 95 85 80 85 95 90 70

Morningglory 30 55 30 25 65 80 60 50 65 20 20 65 50 50

Mustard, Wild - 80 100 100 - 95 100 98 100 85 100 100 100 80

Nightshade 95 70 95 95 - 98 95 85 85 70 90 100 90 75

Nutsedge, Yellow 5 5 20 0 10 5 5 5 5 0 10 10 5 10

Oat, Wild 45 10 40 40 5 35 45 15 15 10 10 50 10 30

Oilseed Rape 98 65 95 90 50 95 85 90 95 80 90 95 95 70

Pigweed - - - - 98 - - - - - - - - -

Pigweed, Palmer 70 70 98 80 - 100 98 80 45 70 50 90 80 40

Poinsettia, Wild 80 70 85 80 - 90 80 75 60 70 65 75 70 50

Ragweed 75 15 60 10 60 35 60 45 55 30 30 35 55 25

Ryegrass, Italian 25 5 20 5 10 20 15 10 10 5 5 30 10 15

Soybean 65 90 35 65 70 95 50 65 75 50 45 60 55 50

Speedwell 98 100 95 100 - 100 90 98 98 80 100 100 85 95 Surinam Grass 30 15 25 20 - 20 15 10 15 10 10 25 10 20

Velvetleaf 80 30 50 40 60 75 70 60 65 35 15 50 65 50

Waterhemp 95 85 98 90 90 100 90 75 75 55 70 100 75 75

Wheat 10 0 10 10 5 10 15 20 15 5 10 20 15 10

Windgrass 30 20 30 50 - 50 35 10 35 30 30 35 35 15

Table C Compounds

31 g ai/ha 7 13 15 16 20 21 22 23 26 33 35 72 73 75

Postemergence

Barnyardgrass 5 10 15 10 10 10 5 10 10 5 5 5 15 -

Blackgrass 0 5 5 0 5 0 0 5 15 5 0 10 5 5

Buckwheat, Wild 60

Canada Thistle 75

Chickweed 5 70 80 20 60 50 60 50 80 55 40 85 80 85

Corn 10 5 10 15 10 5 5 5 25 25 10 15 20 15

Crabgrass, Large 5 15 20 15 10 20 15 10 20 5 10 10 10 10

Field Poppy 80

Field Violet 98

Foxtail, Giant 5 25 30 20 10 10 10 35 10 10 10 30 25 10

Galium 0 50 60 50 60 80 25 55 80 70 35 80 70 70

Geranium, Cutleaf 40

Johnsongrass - - - - - - - 15 20 10 5 10 10 10

Kochia 30 30 95 50 95 50 80 50 90 95 40 100 100 85

Lambsquarters 25 55 75 50 80 60 70 55 90 70 40 85 80 55

Morningglory 25 30 75 30 65 25 10 55 60 65 50 65 75 15

Mustard, Wild

Nightshade 80

Nutsedge, Yellow 0 5 0 5 5 0 0 0 10 5 0 10 15 0

Oat, Wild 0 5 5 5 0 0 0 5 10 10 0 5 5 35

Oilseed Rape 0 35 95 35 50 40 40 5 75 45 30 60 80 80

Pigweed 40 70 90 75 95 75 70 75 98 95 70 85 85 -

Pigweed, Palmer 90

Poinsettia, Wild 70

Ragweed 20 5 40 10 50 10 35 35 55 30 5 50 55 10

Ryegrass, Italian 0 0 5 0 5 0 0 0 5 5 0 5 5 10

Soybean 25 35 45 35 65 40 40 30 55 65 25 70 70 65 Velvetleaf 20 25 50 25 50 60 40 35 55 50 30 50 60 35

Waterhemp 70 - - - 95 85 75 90 98 80 80 80 98 90

Wheat 0 0 0 0 0 0 0 0 0 0 0 0 5 5

Windgrass 5

Table C Compounds

31 g ai/ha 77 79 80 82 89 92 107 110 125 130 136 137 138 143

Postemergence

Barnyardgrass 25 - - 10 - 10 - 10 5 5 5 10 - 10

Blackgrass 20 10 5 35 15 10 20 15 20 5 10 10 35 15

Buckwheat, Wild - 80 70 70 75 - 75 85 65 90 60 75 80 85

Canada Thistle - 65 75 85 80 - 85 90 85 75 75 85 80 85

Chickweed 80 90 75 85 95 100 90 95 75 75 65 55 85 80

Corn 15 25 10 20 15 20 20 20 10 20 10 15 20 20

Crabgrass, Large 25 25 15 30 60 10 10 20 10 10 5 20 65 5

Field Poppy - 98 75 85 95 - 98 100 95 100 85 95 100 90

Field Violet - 75 85 70 100 - 98 95 98 85 90 70 95 80

Foxtail, Giant 20 20 10 10 10 20 10 10 10 10 20 20 20 10

Galium 98 80 75 75 75 85 80 75 70 80 65 70 80 85

Geranium, Cutleaf - 50 35 30 35 - 35 30 30 35 25 25 35 50

Johnsongrass - 65 5 20 10 - 10 10 5 5 5 10 25 5

Kochia 100 80 75 95 75 100 85 100 90 85 80 90 85 100

Lambsquarters 75 85 75 75 75 60 85 90 98 90 75 75 90 90

Morningglory 85 20 35 40 15 85 60 50 45 25 15 15 55 70

Mustard, Wild - - 80 95 - - 90 90 95 90 95 85 100 100

Nightshade - 95 65 80 90 - 90 85 75 80 75 80 80 85

Nutsedge, Yellow 10 5 0 10 0 10 5 5 5 0 0 0 0 5

Oat, Wild 5 60 0 40 10 5 40 30 10 10 5 10 55 10

Oilseed Rape 70 98 60 95 95 50 80 60 85 85 80 95 85 80

Pigweed 98 - - - - 90 - - - - - - - -

Pigweed, Palmer - 80 35 80 75 - 95 95 85 65 55 45 80 75

Poinsettia, Wild - 75 65 65 60 - 75 65 65 70 65 65 60 65

Ragweed 40 20 10 35 5 40 35 50 35 45 20 35 30 50

Ryegrass, Italian 5 30 0 15 5 15 35 10 5 10 5 5 5 10

Soybean 50 70 75 60 40 40 40 40 60 55 40 30 55 40

Speedwell - 90 100 85 100 - 100 95 70 85 80 80 100 80

Surinam Grass - 25 10 20 10 - 25 20 10 10 5 10 20 10

Velvetleaf 50 75 35 45 35 50 65 40 35 45 50 15 35 55 Waterhemp 98 95 80 95 70 85 98 90 80 75 70 60 98 80

Wheat 0 5 0 10 10 0 5 5 5 5 5 5 5 10

Windgrass - 35 5 35 10 - 15 25 15 15 10 10 15 35

Table C Compound Table C Compound

31 g ai/ha 144 31 g ai/ha 144

Postemergence Postemergence

Barnyardgrass 5 Nightshade 75

Blackgrass 10 Nutsedge, Yellow 0

Buckwheat, Wild 55 Oat, Wild 30

Canada Thistle 60 Oilseed Rape 35

Chickweed 55 Pigweed

Corn 15 Pigweed, Palmer 35

Crabgrass, Large 25 Poinsettia, Wild 35

Field Poppy 80 Ragweed 15

Field Violet 65 Ryegrass, Italian 10

Foxtail, Giant 10 Soybean 30

Galium 70 Speedwell 70

Geranium, Cutleaf 20 Surinam Grass 20

Johnsongrass 5 Velvetleaf 30

Kochia 90 Waterhemp 60

Lambsquarters 75 Wheat 5

Morningglory 20 Windgrass 10

Mustard, Wild 70

Table C Compounds

16 g ai/ha 7 13 15 16 20 21 22 23 26 33 35 72 73 75 Postemergence

Barnyardgrass 5 10 20 5 10 10 5 10 10 5 5 5 10

Blackgrass 0 0 0 0 5 0 0 0 10 5 0 5 10 0

Buckwheat, Wild - 45

Canada Thistle - 70

Chickweed 5 40 35 20 60 40 20 5 55 50 5 65 80 60

Corn 5 10 15 5 5 5 5 5 20 20 5 10 10 10

Crabgrass, Large 5 5 30 10 10 10 10 10 10 5 10 10 15 10

Field Poppy - 70

Field Violet - 80

Foxtail, Giant 5 10 25 10 10 10 10 10 10 5 5 30 15 10

Galium 0 65 70 45 70 55 10 50 55 50 35 80 70 40 Geranium, Cutleaf 30

Johnsongrass - - - - - - - 0 10 10 0 5 5 5

Kochia 0 30 90 40 95 60 50 5 90 90 5 100 98 75

Lambsquarters 5 50 70 40 65 65 65 25 75 60 50 75 75 50

Morningglory 5 20 65 5 75 10 5 10 65 55 40 75 70 5

Mustard, Wild

Nightshade 75

Nutsedge, Yellow 0 5 0 0 0 0 0 0 5 5 0 5 5 0

Oat, Wild 0 0 5 0 0 0 0 5 10 5 0 5 5 5

Oilseed Rape 0 0 45 15 50 30 35 5 40 35 20 50 5 60

Pigweed 35 75 90 50 85 85 60 60 75 95 80 80 90 -

Pigweed, Palmer 75

Poinsettia, Wild 65

Ragweed 10 5 30 20 30 10 5 15 40 40 0 35 50 5

Ryegrass, Italian 10 0 0 0 0 0 0 0 5 0 0 5 5 0

Soybean 25 30 45 15 25 30 40 20 65 25 25 60 45 50

Speedwell 90

Surinam Grass 10

Velvetleaf 5 20 50 20 20 40 50 10 30 25 40 40 40 30

Waterhemp 35 - - - 75 75 75 80 95 90 65 85 85 85

Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Windgrass 0

Table C Compounds

16 g ai/ha 77 79 80 82 89 92 107 110 125 130 136 137 138 143

Postemergence

Barnyardgrass 15 - - 10 - 10 - 10 5 5 5 10 - 5

Blackgrass 5 20 0 30 10 5 5 10 10 5 5 5 5 10

Buckwheat, Wild - 75 70 80 70 - 45 85 70 35 50 70 70 75

Canada Thistle - 55 75 85 80 - 80 65 80 75 65 75 80 85

Chickweed 80 95 60 55 65 100 80 60 70 75 55 70 75 80

Corn 15 15 15 20 15 10 10 10 10 10 5 10 15 15

Crabgrass, Large 10 10 10 10 55 20 10 10 10 5 5 10 35 5

Field Poppy - 85 70 50 90 - 80 85 90 100 65 85 100 80

Field Violet - 70 75 60 100 - 95 80 90 80 85 65 90 75

Foxtail, Giant 10 10 5 10 10 10 10 10 10 10 10 20 10 20

Galium 75 75 70 50 75 80 75 60 65 75 50 55 65 75

Geranium, Cutleaf - 45 30 30 35 - 25 5 25 25 15 10 30 30 Johnsongrass - 40 5 5 5 - 20 5 5 5 5 5 10 5

Kochia 95 75 55 80 70 100 80 95 85 80 80 85 75 98

Lambsquarters 55 75 50 70 70 40 80 75 70 75 55 55 65 75

Morningglory 50 10 25 25 5 20 20 30 20 10 10 10 10 15

Mustard, Wild - - 75 95 100 - 85 90 90 98 85 100 100 100

Nightshade - 90 60 85 75 - 75 75 50 75 70 60 75 65

Nutsedge, Yellow 5 0 0 10 0 0 5 0 5 0 0 0 0 0

Oat, Wild 0 15 0 25 15 5 5 20 5 5 5 5 10 10

Oilseed Rape 10 80 50 70 60 5 65 60 80 70 65 90 70 85

Pigweed 95 - - - - Po O

Pigweed, Palmer - 60 30 75 55 90 75 40 35 50 20 75 45

Poinsettia, Wild - 30 65 40 55 - 70 40 65 55 40 15 30 55

Ragweed 40 30 5 40 0 35 25 40 5 25 20 20 0 20

Ryegrass, Italian 0 5 0 5 5 10 5 5 5 5 0 5 5 5

Soybean 25 60 60 25 35 30 50 40 25 40 30 20 35 30

Speedwell - 85 90 75 95 - 100 60 55 80 75 75 95 80

Surinam Grass - 25 10 20 10 - 10 15 5 10 5 5 20 5

Velvetleaf 35 30 30 35 20 35 60 50 20 25 20 10 10 35

Waterhemp 95 95 80 65 70 80 95 85 75 65 70 40 98 75

Wheat 0 5 0 5 0 0 5 5 5 10 0 5 5 5

Windgrass - 20 0 10 10 5 20 10 10 5 10 0 30

Table C Compound Table C Compound

16 g ai/ha 144 16 g ai/ha 144

Postemergence Postemergence

Barnyardgrass 5 Nightshade 65

Blackgrass 10 Nutsedge, Yellow 0

Buckwheat, Wild 70 Oat, Wild 20

Canada Thistle 90 Oilseed Rape 35

Chickweed 50 Pigweed -

Corn 15 Pigweed, Palmer 25

Crabgrass, Large 10 Poinsettia, Wild 30

Field Poppy 60 Ragweed 10

Field Violet 60 Ryegrass, Italian 5

Foxtail, Giant 5 Soybean 30

Galium 50 Speedwell 60

Geranium, Cutleaf 15 Surinam Grass 10

Johnsongrass 5 Velvetleaf 25 Kochia 85 Waterhemp 35

Lambsquarters 40 Wheat 5

Morningglory 30 Windgrass 10

Mustard, Wild 70

Table C Compound Table C Compound

8 g ai/ha 13 4 g ai/ha 13

Postemergence Postemergence

Barnyardgrass 5 Barnyardgrass 5

Blackgrass 0 Blackgrass 0

Chickweed 5 Chickweed 5

Corn 5 Corn 5

Crabgrass, Large 5 Crabgrass, Large 5

Foxtail, Giant 5 Foxtail, Giant 5

Galium 5 Galium 10

Kochia 5 Kochia 0

Lambsquarters 60 Lambsquarters 30

Morningglory 5 Morningglory 5

Nutsedge, Yellow 0 Nutsedge, Yellow 0

Oat, Wild 0 Oat, Wild 0

Oilseed Rape 0 Oilseed Rape 0

Pigweed 60 Pigweed 30

Ragweed 5 Ragweed 5

Ryegrass, Italian 0 Ryegrass, Italian 0

Soybean 20 Soybean 15

Velvetleaf 15 Velvetleaf 15

Wheat 0 Wheat 0

Table C Compounds

125 g ai/ha 15 16 20 21 26 30 33 61 72 73 75 77 79 80

Preemergence

Barnyardgrass 100 75 85 98 100 25 100 65 100 100 100 100 95 100

Blackgrass 80 10 100 90 90 0 90 5 100 100 75 100 90 90

Corn 25 10 30 20 40 5 10 0 60 50 5 35 30 20

Crabgrass, Large 100 100 100 100 100 98 100 90 100 100 98 100 98 98

Foxtail, Giant 100 100 100 90 98 75 100 65 100 100 98 100 98 100

Galium - - 95 100 100 85 95 15 100 100 0 98 5 98

Johnsongrass - - - - 98 15 35 20 100 95 70 - 70 60 Kochia - - - - - - - 30 - - 100 - 100 100

Lambsquarters 95 50 90 70 95 55 85 60 100 100 70 98 85 98

Morningglory 60 25 10 10 95 35 40 0 95 75 10 65 60 75

Nightshade - - - - - - - 75 - - 80 - 95 90

Nutsedge, Yellow 50 0 10 0 45 5 5 0 0 10 20 30 0 35

Oat, Wild - - - - - - - 5 - - 5 - 40 30

Oilseed Rape 100 100 50 100 100 100 100 10 100 65 40 100 95 100

Pigweed 100 95 100 100 100 100 100 - 100 100 - 100 - -

Pigweed, Palmer - - - - - - - 75 - - 100 - 90 98

Poinsettia, Wild - - - - - - - 0 - - 35 - 40 85

Ragweed 20 0 0 0 50 0 50 30 45 25 5 45 30 20

Ryegrass, Italian 50 5 70 90 95 5 85 5 100 100 15 90 35 25

Soybean 55 5 10 0 - 60 30 10 90 40 50 25 5 85

Surinam Grass - - - - - - - 25 - - 80 - 85 98

Velvetleaf 100 75 50 100 100 40 100 5 100 95 25 100 75 100

Waterhemp 100 100 98 98 100 100 100 100 100 100 98 100 100 100

Wheat 5 0 5 0 15 10 5 10 80 70 10 0 15 15

Windgrass - - - - - - - 70 - - 100 - 100 100

Table C Compounds

125 g ai/ha 82 89 92 107 125 130 136 138 143 144

Preemergence

Barnyardgrass 90 100 100 100 - - - 95 - 95

Blackgrass 5 90 100 90 90 85 95 90 75 30

Corn 5 10 40 45 5 25 5 5 20 30

Crabgrass, Large 98 98 100 100 100 100 100 98 100 100

Foxtail, Giant 98 85 100 98 100 100 100 100 100 100

Galium 80 0 - 95 80 90 90 5 80 55

Johnsongrass 85 60 - 80 75 85 70 60 80 70

Kochia 95 90 - 100 98 98 98 80 90 100

Lambsquarters 70 65 100 95 95 95 80 70 95 75

Morningglory 10 20 70 85 50 10 30 10 25 20

Nightshade 85 85 - 90 - - - 80 - 100

Nutsedge, Yellow 0 0 50 0 5 0 5 0 5 70

Oat, Wild 5 10 - 65 55 60 45 30 5 10

Oilseed Rape 50 15 100 98 80 95 98 20 98 90

Pigweed - - 100 - - - - - - -

Pigweed, Palmer 100 98 - 100 100 85 100 100 100 100 Poinsettia, Wild 20 40 - 70 30 45 50 50 25 80

Ragweed 30 50 60 50 35 10 40 10 5 10

Ryegrass, Italian 5 40 95 90 85 70 65 80 45 60

Soybean 0 10 60 45 20 30 40 5 20 60

Surinam Grass 35 75 - 98 65 80 100 75 50 60

Velvetleaf 10 60 100 98 65 85 65 50 70 45

Waterhemp 100 100 100 100 100 100 100 98 100 100

Wheat 0 5 20 35 5 0 10 10 0 5

Windgrass 90 100 - 100 100 100 100 100 100 90

Table C Compounds

62 g ai/ha 15 16 20 21 26 30 33 61 72 73 75 77 79 80

Preemergence

Barnyardgrass 100 30 30 90 100 10 95 50 80 100 80 98 75 70

Blackgrass 50 5 85 55 90 0 70 0 98 100 80 90 75 70

Corn 10 0 0 5 25 0 10 10 20 40 0 20 5 5

Crabgrass, Large 100 90 98 98 100 80 100 75 100 100 98 100 100 100

Foxtail, Giant 100 90 90 95 98 65 98 60 75 100 65 100 80 85

Galium - - 80 5 95 60 60 10 90 100 5 98 70 75

Johnsongrass - - - - 80 0 25 0 70 80 30 - 50 55

Kochia - - - - - - - 5 - - 90 - 90 100

Lambsquarters 85 20 10 25 95 30 80 50 90 90 35 100 70 95

Morningglory 35 25 5 5 85 10 25 0 55 60 20 35 10 40

Nightshade - - - - - - - 50 - - 75 - 80 85

Nutsedge, Yellow 5 0 0 0 15 0 5 0 0 0 0 0 0 0

Oat, Wild - - - - - - - 5 - - 0 - 5 10

Oilseed Rape 100 60 50 75 100 100 85 0 80 50 10 100 70 70

Pigweed 100 50 100 98 100 100 100 - 100 100 - 100 - -

Pigweed, Palmer - - - - - - - 70 - - 95 - 90 100

Poinsettia, Wild - - - - - - - 0 - - 35 - 10 40

Ragweed 30 5 0 0 60 0 40 5 40 10 0 40 20 5

Ryegrass, Italian 15 5 30 15 85 0 30 0 45 85 5 35 30 5

Soybean 40 0 0 0 35 10 - 20 15 25 10 15 5 40

Surinam Grass - - - - - - - 60 - - 35 - 50 60

Velvetleaf 100 50 5 70 85 10 55 5 55 75 35 70 20 70

Waterhemp 100 85 100 95 100 100 100 90 100 100 98 100 95 100

Wheat 0 0 0 0 5 0 0 5 30 30 10 0 5 0

Windgrass - - - - - - - 40 - - 100 - 100 100 Table C Compounds

62 g ai/ha 82 89 92 107 125 130 136 138 143 144

Preemergence

Barnyardgrass 20 90 98 100 - - - 80 - 70

Blackgrass 5 85 100 90 60 60 60 80 80 40

Corn 0 0 35 15 5 5 5 5 0 5

Crabgrass, Large 90 100 100 100 100 100 100 98 100 100

Foxtail, Giant 90 60 100 98 98 98 70 85 100 100

Galium 0 0 - 90 30 90 50 5 80 50

Johnsongrass 40 30 - 70 60 70 35 50 50 40

Kochia 90 85 - 100 90 65 85 80 90 100

Lambsquarters 20 0 100 85 60 35 25 25 95 65

Morningglory 0 5 60 40 10 20 5 0 5 10

Nightshade 40 65 - 80 - - - 80 - 90

Nutsedge, Yellow 0 0 5 0 0 0 0 0 0 60

Oat, Wild 5 30 - 30 10 35 5 5 5 10

Oilseed Rape 5 0 100 85 50 40 70 5 80 5

Pigweed - - 100 - - - - - - -

Pigweed, Palmer 100 90 - 100 100 100 100 100 100 100

Poinsettia, Wild 0 20 - 40 25 10 25 5 20 40

Ragweed 20 5 60 50 5 5 0 0 0 0

Ryegrass, Italian 5 15 55 70 40 60 35 20 30 0

Soybean 0 5 70 35 0 10 15 0 15 30

Surinam Grass 25 65 - 98 40 65 10 65 35 70

Velvetleaf 0 25 100 98 60 75 15 20 40 15

Waterhemp 100 100 100 100 100 100 100 100 100 98

Wheat 0 0 0 15 0 5 0 5 0 0

Windgrass 80 65 - 100 90 100 85 100 100 80

Table C Compounds

31 g ai/ha 13 15 16 20 21 26 30 33 61 72 73 75 77

Preemergence

Barnyardgrass 40 85 15 5 55 75 15 40 0 90 80 60 60

Blackgrass 0 0 0 40 35 90 0 10 0 98 98 5 15 10

Corn 10 0 0 0 0 0 0 0 0 20 20 0 15 0

Crabgrass, Large 85 100 75 50 75 100 35 98 10 100 100 85 100 98

Foxtail, Giant 95 100 25 50 80 98 30 95 50 80 100 25 100 70

Galium 0 0 90 10 60 0 75 10 0 0 0 Johnsongrass - - - - - 50 0 5 0 65 40 0 - 5

Kochia - - - - - - - - 5 - - 50 - 90

Lambsquarters 15 70 20 5 30 85 25 60 15 80 90 10 60 10

Morningglory 5 20 0 0 0 10 10 0 0 40 10 0 20 10

Nightshade - - - - - - - - 60 - - 75 - 65

Nutsedge, Yellow 5 0 0 0 0 0 0 0 0 0 0 0 0 0

Oat, Wild - - - - - - - - 0 - - 0 - 0

Oilseed Rape 50 100 50 0 0 85 55 80 0 80 20 0 55 0

Pigweed 60 100 0 55 55 100 95 100 - 100 95 - 100 -

Pigweed, Palmer - - - - - - - - 50 - - 100 - 85

Poinsettia, Wild - - - - - - - - 0 - - 40 - 0

Ragweed 10 10 0 0 0 30 0 35 0 0 0 0 0 0

Ryegrass, Italian 0 5 0 0 10 75 0 30 0 45 35 5 30 10

Soybean 5 10 0 0 0 10 - - 20 0 0 0 5 0

Surinam Grass - - - - - - - - 10 - - 30 - 30

Velvetleaf 70 85 5 0 40 30 0 30 5 60 30 5 30 5

Waterhemp 100 100 60 85 75 100 100 100 75 100 100 95 100 98

Wheat 5 0 0 0 0 20 0 0 0 0 0 0 0 5

Windgrass - - - - - - - - 5 - - 45 - 80

Table C Compounds

31 g ai/ha 80 82 89 92 107 125 130 136 138 143 144

Preemergence

Barnyardgrass 30 5 35 85 85 - - - 40 - 40

Blackgrass 10 0 15 80 90 60 30 35 50 75 10

Corn 5 0 0 15 0 0 0 0 0 0 0

Crabgrass, Large 80 70 98 100 98 98 100 85 95 100 98

Foxtail, Giant 40 80 5 100 98 85 70 65 80 98 85

Galium 5 0 0 - 60 5 50 0 0 30 50

Johnsongrass 30 5 40 - 30 5 10 25 0 25 10

Kochia 95 50 60 - 100 60 65 80 75 80 90

Lambsquarters 70 20 0 100 75 30 30 30 35 10 40

Morningglory 20 0 0 40 0 10 5 0 0 0 0

Nightshade 70 20 75 - 60 - - - 50 - 65

Nutsedge, Yellow 0 0 0 5 0 0 0 0 0 0 20

Oat, Wild 0 0 10 - 5 0 15 0 0 0 5

Oilseed Rape 80 0 0 100 40 5 10 5 0 5 0

Pigweed - - - 100 - - - - - - - Pigweed, Palmer 85 85 70 - 100 100 75 75 60 100 100

Poinsettia, Wild 30 0 0 - 10 0 0 5 0 5 5

Ragweed 0 0 0 55 30 10 0 20 0 0 0

Ryegrass, Italian 0 0 5 5 35 30 35 30 10 20 0

Soybean 20 0 5 40 20 0 0 0 0 0 0

Surinam Grass 50 10 35 - 60 20 50 25 65 10 5

Velvetleaf 55 0 20 75 75 5 10 5 25 10 0

Waterhemp 100 50 85 100 98 100 100 100 85 98 98

Wheat 0 0 0 0 10 0 0 0 5 0 -

Windgrass 60 30 50 - 100 85 70 30 100 85 30

Table C Compounds

16 g ai/ha 13 15 16 20 21 26 30 33 61 72 73 75 77 79

Preemergence

Barnyardgrass 10 10 0 0 10 40 10 20 0 25 15 5 20 5

Blackgrass 0 0 0 0 5 45 0 0 0 60 5 0 5 5

Corn 5 0 0 0 0 0 0 0 0 5 0 0 0 0

Crabgrass, Large 60 95 5 5 20 98 0 75 0 100 98 65 98 65

Foxtail, Giant 0 100 5 35 20 95 5 60 0 55 98 0 95 40

Galium - - - 10 - 5 80 0 0 5 5 0 0 0

Johnsongrass - - - - - 55 0 0 0 5 0 0 - 0

Kochia - - - - - - - - 0 - - 0 - 5

Lambsquarters 50 60 0 0 0 70 10 25 5 65 85 0 50 0

Morningglory 5 20 10 0 0 20 0 0 0 10 0 0 10 20

Nightshade - - - - - - - - 60 - - 40 - 30

Nutsedge, Yellow 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Oat, Wild - - - - - - - - 0 - - 0 - 0

Oilseed Rape 0 30 0 0 0 80 10 50 0 5 0 0 0 0

Pigweed 5 98 0 55 5 100 90 80 - 100 90 - 85 -

Pigweed, Palmer - - - - - - - - 40 - - 70 - 75

Poinsettia, Wild - - - - - - - - 0 - - 10 - 0

Ragweed 0 10 0 0 0 20 0 55 0 0 0 0 0 0

Ryegrass, Italian 0 0 0 0 0 35 0 0 0 10 30 0 0 0

Soybean 5 0 0 0 0 - 0 15 - 0 0 0 5 0

Surinam Grass - - - - - - - - 0 - - 0 - 5

Velvetleaf 20 60 0 0 10 0 0 5 0 10 0 0 10 10

Waterhemp 80 90 10 30 70 100 85 100 50 100 65 75 95 100

Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Windgrass - - - - - - 0 - - 5

Table C Compounds

16 g ai/ha 80 82 89 92 107 125 130 136 138 143 144

Preemergence

Barnyardgrass 10 5 5 35 65 - - - 20 - 10

Blackgrass 5 0 5 45 60 5 30 0 10 5 5

Corn 0 0 0 0 0 0 5 0 0 5 0

Crabgrass, Large 55 60 75 100 98 35 98 50 75 70 85

Foxtail, Giant 5 20 0 100 60 30 50 25 35 20 70

Galium 0 0 0 - 5 0 0 0 0 0 0

Johnsongrass 5 0 0 - 10 5 10 10 0 5 0

Kochia 70 0 60 - 100 5 10 50 5 30 70

Lambsquarters 30 30 0 90 30 10 35 25 0 5 50

Morningglory 5 0 0 10 0 0 0 0 0 0 0

Nightshade 55 5 10 - 30 - - - 40 - 35

Nutsedge, Yellow 0 0 0 0 0 0 5 0 0 0 0

Oat, Wild 0 0 5 - 0 5 0 0 0 0 0

Oilseed Rape 35 0 0 85 5 0 0 5 0 0 0

Pigweed - - - 100 - - - - - - -

Pigweed, Palmer 100 55 65 - 100 90 85 95 40 65 85

Poinsettia, Wild 5 0 0 - 0 0 0 0 0 5 0

Ragweed 0 0 0 30 0 0 0 0 0 0 0

Ryegrass, Italian 0 0 0 5 10 0 15 5 0 5 0

Soybean 0 0 0 0 0 0 0 0 0 0 0

Surinam Grass 10 40 10 - 15 5 10 0 30 5 10

Velvetleaf 30 0 10 50 40 10 5 0 5 0 0

Waterhemp 95 60 70 100 100 70 50 65 75 85 98

Wheat 0 0 0 0 5 0 0 0 0 0 0

Windgrass 5 40 60 80 20 30 0 70 25 0

Table C Compound Table C Compound

8 g ai/ha 13 4 g ai/ha 13

Preemergence Preemergence

Barnyardgrass 0 Barnyardgrass 0

Blackgrass 0 Blackgrass 0

Corn 0 Corn 0

Crabgrass, Large 30 Crabgrass, Large 25

Foxtail, Giant 0 Foxtail, Giant 0 Lambsquarters 5 Lambsquarters 0

Morningglory 0 Morningglory 0

Nutsedge, Yellow 0 Nutsedge, Yellow 0

Oilseed Rape 0 Oilseed Rape 0

Pigweed 10 Pigweed 5

Ragweed 0 Ragweed 0

Ryegrass, Italian 0 Ryegrass, Italian 0

Soybean 0 Soybean 0

Velvetleaf 10 Velvetleaf 5

Waterhemp 10 Waterhemp 5

Wheat 0 Wheat 0

Table C Compounds Table C Compounds

250 g ai/ha 61 66 92 119 125 g ai/ha 61 62 66 92 119

Flood Flood

Barnyardgrass 40 80 40 25 Barnyardgrass 20 20 25 20 0

Ducksalad 90 95 100 50 Ducksalad 90 75 85 95 40

Rice 20 20 15 0 Rice 20 10 0 15 0

Sedge, Umbrella 85 95 100 90 Sedge, Umbrella 85 65 85 90 80

Table C Compounds Table C Compounds

62 g ai/ha 61 62 66 92 119 31 g ai/ha 61 62 66 92 119

Flood Flood

Barnyardgrass 0 0 0 0 0 Barnyardgrass 0 0 0 0 0

Ducksalad 75 40 80 60 0 Ducksalad 50 0 40 30 0

Rice 20 0 0 15 0 Rice 20 0 0 10 0

Sedge, Umbrella 80 60 75 60 55 Sedge, Umbrella 80 0 40 20 0

Table C Compound

16 g ai/ha 62

Flood

Barnyardgrass 0

Ducksalad 0

Rice 0

Sedge, Umbrella 0