ZA200206148B

ZA200206148B - Insecticidal anthranilamides.

Info

Publication number: ZA200206148B
Application number: ZA200206148A
Authority: ZA
Inventors: George P Lahm; Brian J Myers; Thomas Paul Selby; Thomas Martin Stevenson
Original assignee: Du Pont
Priority date: 2000-03-22
Filing date: 2002-08-01
Publication date: 2003-11-05

Description

: IITLE

INSECTICIDAL ANTHRANILAMIDES

BACKGROUND OF THE INVENTION

. This invention relates to certain anthranilamides, their N-oxides, agriculturally suitable salts and compositions, and methods of their use as arthropodicides in both . agronomic and nonagronomic environments.

The control of arthropod pests is extremely important in achieving high crop : efficiency. Arthropod damage to growing and stored agronomic crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. The control of arthropod pests in forestry, greenhouse crops, ornamentals, nursery crops, stored food and fiber products, livestock, household, and public and animal health 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 modes of action.

NL 9202078 discloses N-acyl anthranilic acid derivatives of Formula i as insecticides

Rr? RS 0 . - Rr?

R> LN RS

R? ©

Rl Zz i wherein, inter alia,

X is a direct bond;

Y is H or C;-Cg alkyl;

Z is NH, NH(C;-C5 alkyl) or N(C{-Cj3 alkyl),; and

R! through R? are independently H, halogen, C;-Cg alkyl, phenyl, hydroxy, C;-Cg alkoxy or C1-C; acyloxy. ’ SUMMARY OF THE INVENTION

This invention pertains to a method for controlling arthropods comprising contacting ) 25 the arthropods or their environment with an arthropodicidally effective amount of a compound of Formula 1, its N-oxide or agriculturally suitable salts 1 i

A J

3 RN

Ree « 4 B . R27 TNS 1 wherein

A and B are independently O or S; each J is independently a phenyl or naphthyl group substituted with 1 to 2 RS and 5 optionally substituted with 1 to 3 RS; or each J is independently a 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system wherein each ring or ring system is optionally substituted with 1 to 4 R7; nis 1 to 4;

Rl is H; or Cy-Cg alkyl, C»-Cg alkenyl, C,-Cg alkynyl or C3-C¢ cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO,, hydroxy, C;-C, alkoxy, C;-C, alkylthio, C;-Cy4 alkylsulfinyl, C;-C, alkylsulfonyl, C,-C, alkoxycarbonyl, C;-C, alkylamino,

C,-Cjg dialkylamino and C3-Cg cycloalkylamino; or

R1 is C,-Cg alkylcarbonyl, C,-Cg alkoxycarbonyl, C,-Cy alkylaminocarbonyl, C;3-Cg dialkylaminocarbony! or C(=A)J;

R2 is H, Cy-Cg alkyl, C,-Cg alkenyl, C»-Cg alkynyl, C3-Cg cycloalkyl, C;-C, alkoxy,

C,-C4 alkylamino, C,-Cg dialkylamino, C3-Cg4 cycloalkylamino, Co-Cg alkoxycarbonyl or C5-C¢ alkylcarbonyl;

R3 is H; G; C1-Cg alkyl, C,-Cg alkenyl, C,-Cg alkynyl, C3-Cg cycloalkyl, each optionally substituted with one or more substituents selected from the group consisting of halogen, G, CN, NO, hydroxy, C;-C4 alkoxy, C;-C4 haloalkoxy,

C;-C4 alkylthio, C;-C,4 alkylsulfinyl, C;-C, alkylsulfonyl, C,-Cg alkoxycarbonyl, C,-Cg4 alkylcarbonyl, C3-Cg trialkylsilyl, or a phenyl, phenoxy or 5- or 6-membered heteroaromatic ring, each ring optionally substituted with ) one to three substituents independently selected from the group consisting of C;-

C4 alkyl, C,-C4 alkenyl, C5-Cy4 alkynyl, C3-Cg cycloalkyl, C1-C4 haloalkyl, C,- ) C4 haloalkenyl, C,-Cy4 haloalkynyl, C3-Cg halocycloalkyl, halogen, CN, NO,,

C;-Cy alkoxy, C;-Cy4 haloalkoxy, C;-Cy alkylthio, C,-Cy alkylsulfinyl, C;-C, alkylsulfonyl, C;-C4 alkylamino, C,-Cg dialkylamino, C3-Cg cycloalkylamino,

C3-Cg (alkyl)cycloalkylamino, C,-Cy4 alkylcarbonyl, C5-Cg alkoxycarbonyl, C,-

Cg alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl or C3-Cg trialkylsilyl; Cq-

C4 alkoxy; C;-Cy alkylamino; C,-Cg dialkylamino; C3-Cg4 cycloalkylamino; Co- ‘ C¢ alkoxycarbonyl or C,-Cg alkylcarbonyl; or

R2 and R3 can be taken together with the nitrogen to which they are attached to form . a ring containing 2 to 6 atoms of carbon and optionally one additional atom of nitrogen, sulfur or oxygen, said ring may be optionally substituted with 1 to 4 substituents selected from the group consisting of C;~C, alkyl, halogen, CN,

NO; and C4-C, alkoxy;

G is a 5- or 6-membered nonaromatic carbocyclic or heterocyclic ring, optionally including one or two ring members selected from the group consisting of C(=0),

SO or S(O), and optionally substituted with 1 to 4 substituents selected from the group consisting of C4-C, alkyl, halogen, CN, NO, and C;-C, alkoxy; each R* is independently H, C;-Cg alkyl, C,-Cg alkenyl, C,-Cg¢ alkynyl, C3-Cg cycloalkyl, C-Cg haloalkyl, C,-Cg haloalkenyl, C5-Cg haloalkynyl, C3-Cg halocycloalkyl, halogen, CN, NO, hydroxy, C;-C4 alkoxy, C;-C4 haloalkoxy,

C-C4 alkylthio, C;-C4 alkylsulfinyl, C;-C4 alkylsulfonyl, C;-C4 haloalkylthio,

C1-C4 haloalkylsulfinyl, C{-C,4 haloalkylsulfonyl, C{-C,4 alkylamino, C,-Cg dialkylamino, C3-Cg4 cycloalkylamino, or C3-Cyg trialkylsilyl; or each R* is independently phenyl, benzyl or phenoxy, each optionally substituted with

C;-C4 alkyl, C5-Cy4 alkenyl, C,-C4 alkynyl, C3-Cg cycloalkyl, C{-Cy4 haloalkyl,

C,-Cy4 haloalkenyl, C,-C4 haloalkynyl, C3-Cg halocycloalkyl, halogen, CN,

NO,, Cy-C, alkoxy, C1-C4 haloalkoxy, C;-C4 alkylthio, C-C4 alkylsulfinyl, Cy-

C4 alkylsulfonyl, Cy-C4 alkylamino, C,-Cg dialkylamino, C3-Cg cycloalkylamino, C3-Cg (alkyl)cycloalkylamino, C5-Cy4 alkylcarbonyl, C5-Cg alkoxycarbonyl, C,-Cg alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl or Cs-

Cg trialkylsilyl; each RS is independently C;-Cg4 alkyl, C5-Cg¢ alkenyl, C5-Cg alkynyl, C3-Cg cycloalkyl, C;-Cg haloalkyl, C,-Cg¢ haloalkenyl, C,-C¢ haloalkynyl, C3-Cg halocycloalkyl, halogen, CN, CO,H, CONH,, NO,, hydroxy, C;-Cg4 alkoxy,

C;-Cg haloalkoxy, C;-Cg alkylthio, C;-Cg alkylsulfinyl, C;-Cg alkylsulfonyl,

C;-Cg haloalkylthio, C;-Cg haloalkylsulfinyl, C{-C¢ haloalkylsulfonyl, Ci-Cq . alkylamino, C,-C1, dialkylamino, or C3-Cg4 cycloalkylamino, C5-Cg alkylcarbonyl, C,-Cg alkoxycarbonyl, C,-C¢ alkylaminocarbonyl, C3-Cg

J 35 dialkylaminocarbonyl, C5-Cy trialkylsilyl; or (R3), when attached to adjacent carbon atoms can be taken together as -OCF,0-, -CF,CF50-, or -OCF,CF50-;

each RS is independently H, halogen, C;-Cg alkyl, C,-Cg alkenyl, C,-Cg alkynyl, C3-

Cg cycloalkyl, C1-Cy4 alkoxy or C,-C4 alkoxycarbonyl; or each RS is independently a phenyl, benzyl, phenoxy, 5- or 6-membered , heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system, each ring optionally substituted with one to three substituents . independently selected from the group consisting of C;-Cy4 alkyl, C,-C, alkenyl,

C,-C4 alkynyl, C3-Cq cycloalkyl, C;-Cy4 haloalkyl, C,-C, haloalkenyl, Co-Cy4 haloalkynyl, C3-Cg halocycloalkyl, halogen, CN, NO,, C;-C, alkoxy, C;-C4 haloalkoxy, C1-Cy alkylthio, C;-C, alkylsulfinyl, C;-C, alkylsulfonyl, C{-C4 alkylamino, C,-Cjg dialkylamino, C3-Cg cycloalkylamino, C3-Cg (alkylcycloalkylamino, C,-Cy alkylcarbonyl, C,-Cg alkoxycarbonyl, C,-Cg alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl or C3-Cg trialkylsilyl; each R7 is independently H, C;-Cg alkyl, C,-Cg alkenyl, C,-Cg alkynyl, C5-Cg cycloalkyl, C;-Cg haloalkyl, C,-Cg haloalkenyl, C,-Cg haloalkynyl, C5-Cg halocycloalkyl, halogen, CN, CO,H, CONH,, NO,, hydroxy, C-C, alkoxy,

C1-C4 haloalkoxy, C1-C4 alkylthio, C1~Cy alkylsulfinyl, C;-C alkylsulfonyl,

C;-C4 haloalkylthio, C;-C,4 haloalkylsulfinyl, C;-C4 haloalkylsulfonyl, C;-Cy alkylamino, C,-Cg dialkylamino, C3-Cg cycloalkylamino, C,-Cg alkylcarbonyl,

C,-Cg alkoxycarbonyl, C,-Cg4 alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl,

C3-Cg trialkylsilyl; or each R7 is independently a phenyl, benzyl, benzoyl, phenoxy, 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system, each ring optionally substituted with one to three substituents independently selected from the group consisting of C1-C4 alkyl, C,-C, alkenyl,

C,-C4 alkynyl, C3-Cg cycloalkyl, C;-Cy4 haloalkyl, C,-Cy4 haloalkenyl, C,-Cy4 haloalkynyl, C3-Cg halocycloalkyl, halogen, CN, NO,, C1-C4 alkoxy, C;-Cy4 haloalkoxy, C;-C, alkylthio, C;-Cy alkylsulfinyl, C;-C, alkylsulfonyl, C;-C, alkylamino, C,-Cg dialkylamino, C3-Cg cycloalkylamino, C3-Cg (alkyl)cycloalkylamino, C5-Cy4 alkylearbonyl, C,-Cg alkoxycarbonyl, C,-Cg alkylaminocarbonyl, C5-Cg dialkylaminocarbonyl or C-Cg trialkylsilyl; provided that (1) when A and B are both O, R? is H or Cy-C5 alkyl, R3 is H or C;-C; alkyl and R4 . is H, halogen, C;-Cg alkyl, phenyl, hydroxy or C;-Cg alkoxy, then one RS is other than halogen, C;-Cg alkyl, hydroxy or C;-C4 alkoxy; or . 35 (2) J is other than an optionally substituted 1,2,3-thiadiazole.

This invention also pertains to compounds of Formula 1, their N-oxides and agriculturally suitable salts

As I] ®hn ; . B ) 2 R3 : 1 wherein

Rlis H; or C}-Cg alkyl, C5-Cg alkenyl, C»-Cg alkynyl or C3-Cg cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO,, hydroxy, C;-C4 alkoxy, C;-C, alkylthio, C-Cy4 alkylsulfinyl, C;-Cy alkylsulfonyl, Co-C, alkoxycarbonyl, C,-C alkylamino,

C,-Cg dialkylamino and C3-Cg¢ cycloalkylamino; or

R! is C,-Cg alkylcarbonyl, C,-Cg alkoxycarbonyl, C,-Cg alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl or C(=A)J;

R2 is H, C;-Cg alkyl, C,-Cg alkenyl, C5-Cg alkynyl, C5-Cg cycloalkyl, C;-Cy alkoxy,

C,-C4 alkylamino, C,-Cg dialkylamino, C3-Cg cycloalkylamino, C»-Cg alkoxycarbonyl or C,-Cg¢ alkylcarbonyl;

R3 is H; C;-Cg alkyl, C,-Cg alkenyl, C5-Cg alkynyl, C3-Cg cycloalkyl, each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO,, hydroxy, C;-Cy alkoxy, C;-C, haloalkoxy, C;-

C4 alkylthio, Cy-Cy alkylsulfinyl, C;-C, alkylsulfonyl, C,-Cg alkoxycarbonyl,

C,-Cg4 alkylcarbonyl, C3-Cg trialkylsilyl, ora phenoxy ring optionally substituted with one to three substituents independently selected from the group consisting of Cy-Cy4 alkyl, C,-Cy alkenyl, C,-Cy4 alkynyl, C3-Cg cycloalkyl, C;-Cy haloalkyl, C,-C, haloalkenyl, C,-C, haloalkynyl, C3-C¢ halocycloalkyl, halogen, CN, NO,, C;-C4 alkoxy, C;-Cy4 haloalkoxy, C,-C, alkylthio, C;-C,4 alkylsulfinyl, C;-Cy alkylsulfonyl, C-Cy4 alkylamino, C,-Cy dialkylamino, Cs-

Cs cycloalkylamino, C3-Cg (alkyl)cycloalkylamino, C,-Cy4 alkylcarbonyl, Cy-Cq alkoxycarbonyl, C,-Cg alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl or C3-

Cg trialkylsilyl; C;-C4 alkoxy; C;-Cy4 alkylamino; C,-Cg dialkylamino; C3-Cg cycloalkylamino; C,-Cg alkoxycarbonyl or C,-Cg alkylcarbonyl; or . R2 and R3 can be taken together with the nitrogen to which they are attached to form a ring containing 2 to 6 atoms of carbon and optionally one additional atom of ) nitrogen, sulfur or oxygen, said ring may be optionally substituted with 1 to 4 substituents selected from the group consisting of C;-C, alkyl, halogen, CN, : NO; and C4-C, alkoxy; . each R4 is independently H, C;-Cg alkyl, C,-Cg alkenyl, C,-Cg alkynyl, C3-Cg cycloalkyl, C;-Cg haloalkyl, C,-Cg haloalkenyl, C,-Cq haloalkynyl, C3-Cg halocycloalkyl, halogen, CN, NO, hydroxy, C;-C4 alkoxy, C;-C4 haloalkoxy,

C-C4 alkylthio, C;-Cy4 alkylsulfinyl, C;-C,4 alkylsulfonyl, C;-C4 haloalkylthio,

C;-C4 haloalkylsulfinyl, C,-C,4 haloalkylsulfonyl, C,-C,4 alkylamino, C,-Cg dialkylamino, C3-Cg cycloalkylamino, or C53-Cg trialkylsilyl; or each R#4 is independently phenyl, benzyl or phenoxy, each optionally substituted with

C;-C4 alkyl, C5-C4 alkenyl, C,-Cy alkynyl, C3-Cg4 cycloalkyl, C;-C4 haloalkyl,

C,-C4 haloalkenyl, C,-C4 haloalkynyl, C3-Cg¢ halocycloalkyl, halogen, CN,

NO,, C;-C4 alkoxy, C;-C4 haloalkoxy, C;-C, alkylthio, C,-C,4 alkylsulfinyl, C;-

C4 alkylsulfonyl, C{-C4 alkylamino, C,-Cg dialkylamino, C3-Cyg cycloalkylamino, C3-Cg (alkyl)cycloalkylamino, C,-C4 alkylcarbonyl, C,-Cg alkoxycarbonyl, C,-Cg alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl or Cs-

Cg trialkylsilyl; each R5 is independently C;-Cg haloalkyl, C,-C¢ haloalkenyl, C,-Cg haloalkynyl,

C5-Cg halocycloalkyl, C,-C4 haloalkoxy, C;-C4 alkylthio, C;-C4 alkylsulfinyl,

C;-C4 alkylsulfonyl, C;-C,4 haloalkylthio, C;-C4 haloalkylsulfinyl, C;-C,4 haloalkylsulfonyl, CN, NO,, C;-C4 alkoxycarbonyl, C;-C4 alkylamino, C,-Cg dialkylamino, C3-Cg4 cycloalkylamino, C,-Cg4 alkylcarbonyl, C5-Cyg alkoxycarbonyl, C,-Cg4 alkylaminocarbonyl, or C3-Cg dialkylaminocarbonyl; or (R5), attached to adjacent carbon atoms can be taken together as -OCF,0-, -CF,CF50-, or -OCF,CF,0-; each RO is independently H, halogen, C1-Cg alkyl, C,-Cg alkenyl, C,-Cg alkynyl, Cs-

Cg cycloalkyl, C1-C4 alkoxy or C,-C, alkoxycarbonyl; or . each RO is independently a phenyl, benzyl, phenoxy, 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic . 35 ring system, each ring optionally substituted with one to three substituents independently selected from the group consisting of C-C4 alkyl, C,-C, alkenyl,

C,-C4 alkynyl, C3-Cg cycloalkyl, C{-C4 haloalkyl, C,-C4 haloalkenyl, C,-C4 : halnallvmvl CAC halaevelaalley] halogen. CN. NOs. C1-Cy alkoxv. C+-Ca haloalkoxy, Cy-Cy alkylthio, C;-Cy4 alkylsulfinyl, C;-C, alkylsulfonyl, C;-Cy4 alkylamino, C,-Cg dialkylamino, C5-Cg cycloalkylamino, C3-Cg (alkyDcycloalkylamino, C5-C4 alkylcarbonyl, C,-Cg alkoxycarbonyl, C»-Cg . alkylaminocarbonyl, C5-Cg dialkylaminocarbonyl or C3-Cg trialkylsilyl; each R7 is independently H, C;-Cg alkyl, C»-Cg alkenyl, C,-Cg alkynyl, C3-Cg . cycloalkyl, C;-Cg haloalkyl, C,-Cg haloalkenyl, C,-Cg haloalkynyl, C3-Cg halocycloalkyl, halogen, CN, CO,H, CONHj, NO,, hydroxy, C;-C, alkoxy,

C1-C4 haloalkoxy, C;-Cy4 alkylthio, C{-C, alkylsulfinyl, C;-C, alkylsulfonyl,

C,-C4 haloalkylthio, C-C4 haloalkylsulfinyl, C;-C,4 haloalkylsulfonyl, C;-Cy4 alkylamino, C,-Cg dialkylamino, C3-Cg cycloalkylamino, C,-Cg alkylcarbonyl,

C,-Cg alkoxycarbonyl, C,-Cg alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl,

C3-Cg trialkylsilyl; or each R7 is independently a phenyl, benzyl, benzoyl, phenoxy or 5- or 6-membered - heteroaromatic ring 8-, 9- or 10-membered fused heterobicyclic ring system, each ring optionally substituted with one to three substituents independently selected from the group consisting of C1-Cy alkyl, C,-C, alkenyl, C,-C, alkynyl,

C3-Cg cycloalkyl, C;-Cy4 haloalkyl, C,-C, haloalkenyl, C,-C4 haloalkynyl, C3-

Cg halocycloalkyl, halogen, CN, NO,, C;-C, alkoxy, C;-C,4 haloalkoxy, C{-Cy alkylthio, C;-C4 alkylsulfinyl, C,-C, alkylsulfonyl, C;-C, alkylamino, C,-Cg dialkylamino, C3-Cg cycloalkylamino, C3-Cg (alkyl)cycloalkylamino, C5-Cy4 alkylcarbonyl, C,-Cg4 alkoxycarbonyl, C,-Cg alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl or C3-Cg trialkylsilyl; provided that (i) at least one R# and at least one R7 are other than H; (ii) J is other than an optionally substituted 1,2,3-thiadiazole; (iii) when J is an optionally substituted pyridine and R2 is H, R3 is other than H or

CHs; (iv) when J is an optionally substituted pyridine, then R7 cannot be CONH,, C,-C alkylaminocarbonyl or C3-Cg dialkylaminocarbonyl; (v) when J is an optionally substituted pyrazole, tetrazole or pyrimidine, then R2 and

R3 cannot both be hydrogen.

This invention also pertains to arthropodicidal compositions comprising an . arthropodicidally effective amount of a compound of Formula 1 and at least one additional component selected from the group consisting of surfactants, solid diluents and liquid . 35 diluents.

DETAILS OF THE INVENTION

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, n-propyl, i-propyl, or the different butyl, pentyl or hexyl isomers. The term “1-2 alkyl” indicates that one or two of the available positions for that substituent may be alkyl. . “Alkenyl” includes straight-chain or branched alkenes such as 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 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, n-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers. “Alkoxyalkyl” denotes alkoxy substitution on alkyl. Examples of “alkoxyalkyl” include CH;0CH,,

CH30CH,CH,, CH3CH,0OCH,, CH3CH,CH,CH,0CH, and CH;CH,0OCH,CHj. “Alkylthio” includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers. “Cycloalkyl” includes, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

The term “heterocyclic ring” or heterocyclic ring system” denotes rings or ring systems in which at least one ring atom is not carbon and comprises 1 to 4 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that each heterocyclic ring contains no more than 4 nitrogens, no more than 2 oxygens and no mote than 2 sulfurs. The heterocyclic ring can be attached through any available carbon or nitrogen by replacement of hydrogen on said carbon or nitrogen. The term “aromatic ring system” denotes fully unsaturated carbocycles and heterocycles in which the polycyclic ring system is aromatic (where aromatic indicates that the Hiickel rule is satisfied for the ring system). The term “heteroaromatic ring” denotes fully aromatic rings in which at least one ring atom is not carbon and comprises 1 to 4 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that each heterocyclic ring contains no more than 4 nitrogens, no more than 2 oxygens and no more than 2 sulfurs (where aromatic indicates that the Hiickel rule is satisfied). The heterocyclic ring can be attached through any available carbon or nitrogen by replacement of hydrogen on said carbon or nitrogen. The term “aromatic heterocyclic ring system” includes fully aromatic ‘ heterocycles and heterocycles in which at least one ring of a polycyclic ring system is aromatic (where aromatic indicates that the Hiickel rule is satisfied). The term “fused : 35 heterobicyclic ring system” includes a ring system comprised of two fused rings in which at least one ring atom is not carbon and can be aromatic or non aromatic, as defined above.

The term “halogen”, either alone or in compound words such as “haloalkyl”, includes flnnrine chlavina hraminae ar indina Toethay when used in comnound words such ag

“haloalkyl”, said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of “haloalkyl” include F5C, CICH,, CF5CH, and

CF3CCly. The terms “haloalkenyl”, “haloalkynyl”, “haloalkoxy”, and the like, are defined ) analogously to the term “haloalkyl”. Examples of “haloalkenyl” include (CI),C=CHCH, and CF3CH,;CH=CHCH,. Examples of “haloalkynyl” include HC=CCHCI, CF5C=C, } CCl;C=C and FCH,C=CCH,. Examples of “haloalkoxy” include CF;0, CCl, CH,O,

HCF,CH,CH,O0 and CF;CH,0. :

The total number of carbon atoms in a substituent group is indicated by the “Ci-Gy” prefix where i and j are numbers from 1 to 6. For example, C;-C3 alkylsulfonyl designates methylsulfonyl through propylsulfonyl; C, alkoxyalkyl designates CH30CH;; C4 alkoxyalkyl designates, for example, CH;CH(OCHj3), CH30CH,CH, or CH;CH,0CHo; 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

CH3CH,CH,OCH,;; and CH3CH,OCH,CH;. In the above recitations, when a compound of

Formula 1 contains a heterocyclic ring, all substituents are attached to this ring through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.

When a group contains a substituent which can be hydrogen, for example R3, then, when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted.

Compounds of this invention can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers. 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. Accordingly, the compounds of the invention may be present as a mixture of stereoisomers, individual stereoisomers, or as an optically active form.

The present invention comprises compounds selected from Formula 1, N-oxides and agriculturally suitable salts thereof. 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 : 35 oxidation of heterocycles and tertiary amines with peroxy acids such as peracetic and m-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides such as - t-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethydioxirane. These methods for the nrenaration of N.axides have been extensively described and reviewed in the 9 y 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 18-19, 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 139-151, 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.

The salts of the compounds of the invention 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.

Of note are certain compounds of Formula II ve; ®m 2 "se: ®n 4 Y 5

RZ” Ng 1 wherein

XandY are O; mis 1to 5; nis 1to4;

R! is H; or C;-Cg alkyl, C,-Cg alkenyl, C,-Cg alkynyl or C3-Cg cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO,, hydroxy, C;-Cy4 alkoxy, C;-C4 alkylthio, C;-C, alkylsulfinyl, C;-C4 alkylsulfonyl, C,-C,4 alkoxycarbonyl, C;-C4 alkylamino,

C,-Cg dialkylamino and C3-Cg cycloalkylamino; or

R1 is C,-Cg alkylcarbonyl, C,-Cg alkoxycarbonyl, C,-Cg alkylaminocarbonyl or

C;-Cg dialkylaminocarbonyl;

R2 is H, C-Cg alkyl, C;-C alkenyl, C,-Cg alkynyl, C3-Cg cycloalkyl, C1-C, alkoxy,

C-C4 alkylamino, C,-Cg dialkylamino, C3-Cg4 cycloalkylamino, C,-Cg alkoxycarbonyl or C-Cg¢ alkylcarbonyl; : R3 is i-propyl or t-butyl; and each R# and R? are independently H, C;-Cg alkyl, C,-Cg alkenyl, C,-Cg alkynyl, . C3-Cg cycloalkyl, C-Cg haloalkyl, C,-Cg haloalkenyl, C,-Cg haloalkynyl,

C3-Cg halocycloalkyl, halogen, CN, CO,H, CONH,, NO,, hydroxy, C;-C4 alkoxy, C1-Cy4 haloalkoxy, C;-C, alkylthio, C,-C, alkylsulfinyl, C;-C, alkylsulfonyl, C;-C, haloalkylthio, C;-Cy4 haloalkylsulfinyl, C;-C,4 haloalkylsulfonyl, Cy-C, alkoxycarbonyl, C;-Cy4 alkylamino, C,-Cg dialkylamino, C3-Cg cycloalkylamino, C,-Cg alkylcarbonyl, C,-Cg alkoxycarbonyl, C,-Cg4 alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl, C3-Cg trialkylsilyl; or each R# and R3 are independently phenyl optionally substituted with C,-C4 alkyl,

C,-C4 alkenyl, C»-Cy4 alkynyl, C3-Cg cycloalkyl, C-C4 haolalkyl, C,-Cy4 haloalkenyl, C,-C4 haloalkynyl, C3-Cg4 halocycloalkyl, halogen, CN, NO,

C1-C4 alkoxy, C;-C4 haloalkoxy, Cy-Cy alkylthio, C1-C4 alkylsulfinyl, C{-C,4 alkylsulfonyl C,-C, alkoxycarbonyl, C;-C4 alkylamino, C,-Cg dialkylamino,

C3-Cg cycloalkylamino, C3-Cg4 (alkyl)cycloalkylamino, C,-C, alkylcarbonyl,

C,-Cg alkoxycarbonyl, C;-Cg4 alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl or C3-Cg trialkylsilyl.

Also of note are methods for controlling arthropods comprising contacting the arthropods or their environment with an arthropodicidally effective amount of a compound of Formula II and insecticidal compositions thereof.

Also of note are certain compounds of Formula III

A J

1 3 Mg ®n

LG

5

RZ” NS R3 . I wherein

A and B are independently O or S;

J is a phenyl group substituted with 1 to 2 RS and optionally substituted with 1 to 3

RS, or a 5- or 6-membered heteroaromatic ring optionally substituted with 1 to 4

R7; . nis 1 to 4;

R!is H; or C;-Cg alkyl, C,-Cg alkenyl, C,-Cg alkynyl or C5-Cg cycloalkyl each . optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO,, hydroxy, C;-C4 alkoxy, C;-C, alkylthio, C;-Cy : alkylsulfinyl, C,-C, alkylsulfonyl, C,-C, alkoxycarbonyl, C{-C4 alkylamino,

C,-Cg dialkylamino and C3-Cg cycloalkylamino; or

R! is C,-Cg alkylcarbonyl, C,-Cg alkoxycarbonyl, C»-Cg alkylaminocarbonyl or

C5-Cg dialkylaminocarbonyl;

R2 is H, C4-Cg alkyl, C,-Cg alkenyl, C5-Cg alkynyl, C3-Cg cycloalkyl, C;-C4 alkoxy,

C,-C4 alkylamino, C,-Cyg dialkylamino, C3-C¢ cycloalkylamino, C»-Cg alkoxycarbonyl or C,-Cg alkylcarbonyl;

R3 is H; or Cy-Cg alkyl, C,-Cg alkenyl, C,-Cg alkynyl or C3-Cg cycloalkyl each : optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO, hydroxy, C;-C4 alkoxy, C;-C4 alkylthio, C;-Cy4 alkylsulfinyl and C;-C, alkylsulfonyl; or

RZ and R3 can be taken together with the nitrogen to which they are attached to form a ring containing 2 to 6 atoms of carbon and optionally one additional atom of nitrogen, sulfur or oxygen, said ring may be optionally substituted with 1 to 4 substituents selected from the group consisting of C;-C, alkyl, halogen, CN,

NO, and C;-C, alkoxy; : each R4 is independently H, C{-Cg alkyl, C,-Cg alkenyl, C,-Cg alkynyl, C3-Cg cycloalkyl, C{-Cg haloalkyl, C,-Cg haloalkenyl, C»-Cg haloalkynyl, C5-Cg halocycloalkyl, halogen, CN, CO,H, CONH,, NO,, hydroxy, C;-Cy alkoxy,

C,-C4 haloalkoxy, C;-C4 alkylthio, C4-C4 alkylsulfinyl, C;-C, alkylsulfonyl,

C,-C4 haloalkylthio, C;-C, haloalkylsulfinyl, C,-C, haloalkylsulfonyl, C{-C,4 alkylamino, C,-Cg dialkylamino, C3-Cgq cycloalkylamino, C,-Cg4 alkylcarbonyl,

C,-Cg alkoxycarbonyl, Co-Cg alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl,

C;3-Cg trialkylsilyl; or each R4 is independently phenyl, benzyl or phenoxy, each optionally substituted with

C;-C4 alkyl, C,-C4 alkenyl, C,-C, alkynyl, C3-Cg cycloalkyl, C;-C,4 haolalkyl,

C5-Cy4 haloalkenyl, C,-C4 haloalkynyl, C3-Cg halocycloalkyl, halogen, CN,

NO,, C;-C4 alkoxy, C{-C4 haloalkoxy, C;-Cy4 alkylthio, C;-Cy alkylsulfinyl,

C-C4 alkylsulfonyl, C;-C4 alkylamino, C,-Cg dialkylamino, C3-Cg - - cycloalkylamino, C3-Cg (alkyl)cycloalkylamino, C»-C4 alkylcarbonyl, C,-Cg

Claims

CLAIMS What is claimed is:

1. A method for controlling arthropods comprising contacting the arthropods or their environment with an arthropodicidally effective amount of a compound of Formula 1, . 5 its N-oxide or agriculturally suitable salts A J 2 Y 3 NO gl Nee 4 B p23 1 wherein A and B are independently O or S; each J is independently a phenyl or naphthyl group substituted with 1 to 2 RS and optionally substituted with 1 to 3 RS; : or-each J is independently a 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system wherein each ring or ring system is optionally substituted with 1 to 4 R7; nis 1to 4; R! is H; or Cy-Cg alkyl, C,-Cg alkenyl, C,-C¢ alkynyl or C3-Cg cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO, hydroxy, C;-C, alkoxy, C;-C4 alkylthio, C;-C,4 alkylsulfinyl, C,-C, alkylsulfonyl, C,-C, alkoxycarbonyl, C;-C4 alkylamino, C,-Cg dialkylamino and C3-Cg cycloalkylamino; or R1 is C,-Cg alkylcarbonyl, C,-Cg alkoxycarbonyl, C-Cg alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl or C(=A)J; R? is H, C1-Cg alkyl, C;-Cg alkenyl, C,-Cg alkynyl, C3-Cg cycloalkyl, C;-Cj alkoxy, ~ C;-Cy4 alkylamino, C,-Cg dialkylamino, C5-Cg cycloalkylamino, C,-Cg alkoxycarbonyl or C,-Cg alkylcarbonyl; R3 is H; G; C;-Cg alkyl, C5-Cg alkenyl, C,-Cg alkynyl, C3-C¢ cycloalkyl, each optionally substituted with one or more substituents selected from the group consisting of halogen, G, CN, NO, hydroxy, C;-C, alkoxy, C;-C,4 haloalkoxy, Ci-Cy alkylthio, Ci-Cy alkylsulfinyl, Ci-Cy alkylsulfonyl, C,-Cg : alkoxycarbonyl, C»-Cg alkylcarbonyl, C3-Cg trialkylsilyl, or a phenyl, phenoxy or 5- or 6-membered heteroaromatic ring, each ring optionally substituted with one to three substituents independently selected from the group consisting of Cq- C4 alkyl, C5-C4 alkenyl, C5-C4 alkynyl, C3-Cg cycloalkyl, C~Cy4 haloalkyl, C,- ‘ C4 haloalkenyl, C,-C,4 haloalkynyl, C3-Cg halocycloalkyl, halogen, CN, NO,, C;-C4 alkoxy, C;-C4 haloalkoxy, C;-Cy4 alkylthio, C;-C, alkylsulfinyl, C;-Cy4 : alkylsulfonyl, C;-C, alkylamino, C,-Cg dialkylamino, C3-Cg cycloalkylamino, C3-Cg (alkyl)cycloalkylamino, C,-Cy alkylcarbonyl, C,-Cg alkoxycarbonyl, Co- Cg alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl or C3-Cg trialkylsilyl; C,- C4 alkoxy; C;-C4 alkylamino; C,-Cg dialkylamino; C3-Cg cycloalkylamino; C,- Cg alkoxycarbonyl or C,-Cg alkylcarbonyl; or R2 and R3 can be taken together with the nitrogen to which they are attached to form a ring containing 2 to 6 atoms of carbon and optionally one additional atom of © nitrogen, sulfur or oxygen, said ring may be optionally substituted with 1 to 4 substituents selected from the group consisting of C;-C, alkyl, halogen, CN, NO; and Cy-C; alkoxy; : G is a 5- or 6-membered nonaromatic carbocyclic or heterocyclic ring, optionally including one or two ring members selected from the group consisting of C(=0), SO or S(O), and optionally substituted with 1 to 4 substituents selected from the group consisting of C;-C, alkyl, halogen, CN, NO, and C;-C, alkoxy;

each R4 is independently H, C;-Cg alkyl, C,-Cg alkenyl, C,-Cg alkynyl, C5-C cycloalkyl, C;-Cg haloalkyl, C»-Cg haloalkenyl, C,-Cg haloalkynyl, C5-Cg halocycloalkyl, halogen, CN, NO,, hydroxy, C;-C, alkoxy, C;-C, haloalkoxy, C,-C4 alkylthio, C1-Cy alkylsulfinyl, C;-C, alkylsulfonyl, C,-C, haloalkylthio, C1-C4 haloalkylsulfinyl, C;-Cy4 haloalkylsulfonyl, C1-C, alkylamino, C,-Cg dialkylamino, C3-Cg cycloalkylamino, or C3-Cg trialkylsilyl; or each R% is independently phenyl, benzyl or phenoxy, each optionally substituted with C1-C4 alkyl, C5-C4 alkenyl, C,-C4 alkynyl, C3-Cg cycloalkyl, C;-C,4 haloalkyl, C,-C4 haloalkenyl, C,~C4 haloalkynyl, C3-C¢ halocycloalkyl, halogen, CN, NO,, C1-C4 alkoxy, C;-Cy4 haloalkoxy, C;-C4 alkylthio, C;-Cy alkylsulfinyl, C;-

C4 alkylsulfonyl, C;-C4 alkylamino, C,-Cg dialkylamino, C3-Cg cycloalkylamino, C3-Cg (alkyl)cycloalkylamino, C,-Cy alkylearbonyl, C,-Cg alkoxycarbonyl, C,-Cg alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl or C-

Cy trialkylsilyl; each R3 is independently C,-Cg alkyl, C,-Cg alkenyl, C,-Cg alkynyl, C3-Cg ) 35 cycloalkyl, C;-Cg haloalkyl, C5-Cg haloalkenyl, C,-Cg haloalkynyl, C3-Cg halocycloalkyl, halogen, CN, CO,H, CONHj,, NO,, hydroxy, C;-Cg alkoxy, C,-Cg haloalkoxy, C;-Cg alkylthio, C;-Cg alkylsulfinyl, C;-Cg alkylsulfonyl,

C1-Cg haloalkylthio, C1-Cg haloalkylsulfinyl, C;-Cg haloalkylsulfonyl, C{-Cg alkylamino, C,-C;, dialkylamino, or C3-Cg cycloalkylamino, C5-Cg alkylcarbonyl, C,-Cg alkoxycarbonyl, C,-Cg alkylaminocarbonyl, C3-Cg ’ dialkylaminocarbonyl, C3-Cy trialkylsilyl; or (R53), when attached to adjacent carbon atoms can be taken together as ~OCF,0-, -CF,CF50-, or -OCF,CF,0-; : each RS is independently H, halogen, C;-Cg alkyl, C5-Cg alkenyl, C,-Cg alkynyl, C3- Cg cycloalkyl, C,-Cy alkoxy or C,5-C,4 alkoxycarbonyl; or each R6 is independently a phenyl, benzyl, phenoxy, 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system, each ring optionally substituted with one to three substituents independently selected from the group consisting of C;-Cy4 alkyl, C,-C4 alkenyl, C,-C, alkynyl, C3-Cq cycloalkyl, C{-Cy haloalkyl, C,-C4 haloalkenyl, C,-C,4 haloalkynyl, C3-C¢ halocycloalkyl, halogen, CN, NO,, C;-C4 alkoxy, C;-C4 haloalkoxy, C{-C4 alkylthio, C{-C4 alkylsulfinyl, C;-C4 alkylsulfonyl, C{-C4 alkylamino, C,-Cg dialkylamino, C3-Cg cycloalkylamino, C3-Cg (alkyl)cycloalkylamino, Co-Cy alkylcarbonyl, C,-Cg¢ alkoxycarbonyl, C,-Cg alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl or C3-Cg trialkylsilyl; . each R7 is independently H, C;-Cg alkyl, C,-Cg alkenyl, C5-Cg¢ alkynyl, C3-Cg cycloalkyl, C;{-Cg haloalkyl, C5-Cg haloalkenyl, C,-Cg haloalkynyl, C3-Cg4 halocycloalkyl, halogen, CN, CO,H, CONH;, NO,, hydroxy, C,-C4 alkoxy, C-C4 haloalkoxy, C;-C4 alkylthio, C4-C4 alkylsulfinyl, C;-C4 alkylsulfonyl, C;-C4 haloalkylthio, C;-C4 haloalkylsulfinyl, C;{-C,4 haloalkylsulfonyl, C;-C4 alkylamino, C,-Cg dialkylamino, C3-Cg cycloalkylamino, C,-Cg alkylcarbonyl, C,-Cg alkoxycarbonyl, C,-Cg¢ alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl, C3-Cg trialkylsilyl; or : each R7 is independently a phenyl, benzyl, benzoyl, phenoxy, 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system, each ring optionally substituted with one to three substituents independently selected from the group consisting of C;-Cy4 alkyl, C5-C, alkenyl, C,-C4 alkynyl, C3-Cg4 cycloalkyl, C;-Cy4 haloalkyl, C,-C4 haloalkenyl, C,-C,4 haloalkynyl, C3-Cg halocycloalkyl, halogen, CN, NO,, C;-C, alkoxy, C,-C, haloalkoxy, C;-Cy alkylthio, C;-C, alkylsulfinyl, C;-Cy alkylsulfonyl, C,-C, alkylamino, C,-Cgq dialkylamino, C3-Cg cycloalkylamino, C3-Cg ) 35 (alkylcycloalkylamino, C,-Cy alkylcarbonyl, C,-Cg alkoxycarbonyl, C,-Cg alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl or C3-Cg trialkylsilyl; -provided that :

(1) when A and B are both O, R? is H or C,-Cj alkyl, R3 is H or C;-C; alkyl and R4 is H, halogen, C;-Cq alkyl, phenyl, hydroxy or C;-C¢ alkoxy, then one RS is other than halogen, C;-Cg alkyl, hydroxy or C;-Cg alkoxy; or (2) I is other than an optionally substituted 1,2,3-thiadiazole (3) J is other than 2-hydroxy-4-trifluoromethylphenyl,

2. The method of Claim 1 wherein J is a phenyl group substituted with 1 to 2 RS and optionally substituted with 1 to 3 RS. :

3. The method of Claim 2 wherein A and B are both O; nis li2; R!is H, C-C, alkyl, C,-Cy alkenyl, C5-C,4 alkynyl, C3-Cg cycloalkyl, C,-Cg allcylcarbonyl or C,-Cg alkoxycarbonyl, R2 is H, C;-Cy alkyl, C5-Cy alkenyl, C5-Cy4 alkynyl, C3-Cg cycloalkyl, Co-Cg allcylcarbonyl or C,-Cg alkoxycarbonyl; : R3 is Cy-Cg alkyl, C-Cg alkenyl, C»-Cg alkynyl or C5-Cg cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, C;-C, alkoxy, C,-C; alkylthio, C;-C; alkylsulfinyl and C;-C, alkylsulfonyl; : one of the R* groups is attached to the phenyl ring at the 2-position or 5-position, and said R# is C;-Cy4 alkyl, C,-C, haloalkyl, halogen, GN, NO,, C;-C, alkoxy, C;- C4 haloalkoxy, C;-Cy alkylthio, C1-C4 alkylsulfinyl, C;-Cy alicylsulfonyl, C;-Cy4 haloalkylthio, C;-C,4 haloalkylsulfinyl, C;-C,4 haloalkylsulfonyl; each R3 is independently C;-Cy4 haloalkyl, CN, NO,, C;-C4 haloalkoxy, C;-Cy4 alkylthio, C1-Cy alkylsulfinyl, C;-Cy alkylsulfonyl, C;-C, haloalkylthio, C;-C, haloalkylsulfinyl, C;-C, haloalkylsulfony! or C,-Cy alkoxycarbonyl; or (R3), when attached to adj acent carbon atoms can be taken together as -OCF,0-, -CF,CF,0- or -OCF,CF,0-; and each RS is independently H, halogen, C;-C, alkyl, C;-C, alkoxy or C,-Cy4 alkoxycarbonyl, or each RO is independently a phenyl! or a 5- or 6-membered heteroaromatic ring, each ring optionally substituted with C,-Cy4 alkyl, C5-C, alkenyl, C,-C, alkynyl, Cs- Cg cycloalkyl, C;-Cy haloalkyl, C,-Cy4 haloalkenyl, C5-Cy haloalkynyl, C5-Cg halocycloalkyl, halogen, CN, NO,, C1-C4 alkoxy, C1-C4 haloalkoxy, Ci-Cy alikcylthio, C1-C4 alkylsulfinyl, C,-Cy4 alkylsulfonyl, C;-Cy alkylamino, C,-Cg dialkylamino, C3-Cq cycloalkylamino, C3-Cg (alkyl)cycloalkylamino, Cy-Cy alkcylearbonyl, C,-Cg4 alkoxycarbonyl, C,-Cg alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl or C3-Cg trialkylsilyl. }

‘4. The method of Claim 3 wherein : 199 Amended Sheet - 2003-11-11 [

R! and R2 are both H; R3 is C;-Cy alkyl optionally substituted with halogen, CN, OCHs, S(0)pCHs; each R4 is independently H, CHs, CF, OCF;, OCHF>, S(0),CF3, S(O)pCHF>, CN or n halogen; . 5 each RS is independently CF3, OCF3, OCHF 2: S(0)pCF3, S(0),CHF,, OCH,CF3, OCF,CHF,, S(0),CH,CFj or S(0),CF,CHF»; each RO is independently H, halogen or methyl; or phenyl, pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted with C,-Cy4 alkyl, C;-C,4 haloalkyl, halogen or CN; and pis 0,1 or2.

5. The method of Claim 4 wherein R3 is i-propyl or t-butyl.

6. The method of Claim 1 wherein J is a 5- or 6-membered heteroaromatic ring optionally substituted with 1 to 4 R7.

7. - The method of Claim 6 wherein J is a 5- or 6-membered heteroaromatic ring selected from the group consisting of J-1, J-2, J-3, J4 and J-5, each J optionally substituted with 1 to 3 R7 — X=Y X=Y Ne Ap Z > R JN v~ z7 ZN VA 11 J-2 I-3 7 xX W “Ny R WZ F sok, PN As, 1Y J-4 J-5 . Qis O, S or NR7; and W, X, Y and Z are independently N or CR”, provided that in J-4 and J-5 at least one of W,X,YorZisN.

8. The method of Claim 6 or 7 wherein A and B are O; nis 1 to 2; Rl is H, C;-C, alkyl, C,-C, alkenyl, C,-C, alkynyl, C,-Cg alkylcarbonyl or Co-Cg ) 25 alkoxycarbonyl; : R2 is H, C;-Cy alkyl, C5-Cy4 alkenyl, C,-C, alkynyl, C5-Cg cycloalkyl, Cp-Cg alkylcarbonyl or C,-Cg alkoxycarbonyl,

R3 is H; or C;-Cg alkyl, C,-Cg alkenyl, C5-Cg alkynyl or C3-Cg4 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, C;-C, alkoxy, C;-C, alkylthio, C;-C, alkylsulfinyl d and C-C, alkylsulfonyl; . 5 one of the R4 groups is attached to the phenyl ring at the 2-position, and said R#4 is C;- X C4 alkyl, C;-C,4 haloalkyl], halogen, CN, NO,, C;-C,4 alkoxy, C;-C,4 haloalkoxy, C,-C4 alkylthio, C;-C4 alkylsulfinyl, C;-C, alkylsulfonyl, C;-C,4 haloalkylthio, C1-C4 haloalkylsulfinyl or C;-C, haloalkylsulfonyl; and each R7 is independently H, Cy-C, alkyl, C;-C4 haloalkyl, halogen, CN, NO,, C;-C4 haloalkoxy, C-Cy4 alkylthio, C;-C4 alkylsulfinyl, C;-C4 alkylsulfonyl, C{-C4 haloalkylthio, C;-C4 haloalkylsulfinyl, C;-C, haloalkylsulfonyl or C,-C4 alkoxycarbonyl; or a phenyl or a 5- or 6-membered heteroaromatic ring, each ring optionally substituted with C;-Cy4 alkyl, C,-C4 alkenyl, C5-C,4 alkynyl, C;3-Cg cycloalkyl, C;-C4 haloalkyl, C,-Cy4 haloalkenyl, C,-Cy4 haloalkynyl, Cs3- Cg halocycloalkyl, halogen, CN, NO,, C;-C4 alkoxy, C1-C4 haloalkoxy, C{-Cy4 alkylthio, C{-C4 alkylsulfinyl, C;-C,4 alkylsulfonyl, C;-C4 alkylamino, C,-Cg dialkylamino, C3-Cg cycloalkylamino, C3-Cg (alkyl)cycloalkylamino, C,-Cy alkylcarbonyl, C,-Cg alkoxycarbonyl, C,-Cgq alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl or C3-Cg trialkylsilyl.

"9. The method of Claim 8 wherein J is selected from the group consisting of pyridine, pyrimidine, pyrazole, imidazole, triazole, thiophene, thiazole and oxazole, furan, isothiazole and isoxazole, each optionally substituted with 1 to 3 R7.

10. The method of Claim 9 wherein J is selected from the group consisting of pyridine, pyrimidine, pyrazole, thiophene and thiazole, each optionally substituted with 1 to 3 R7; R! and R2 are both H; " R3is C;-Cy4 alkyl optionally substituted with halogen, CN, OCHs, S(0),CHg; each R* is independently H, CHj, CF3, OCF3, OCHF», S(0),CF3, S(0),CHF,, CN or halogen; : each R7 is independently H, halogen, CH3, CF, OCHF,, S(O),CF3, S(0)pCHF>, OCH, CF3, OCF,CHF, 8(0),CH,CF3, S(0),CF,CHF; or phenyl, pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted with C1-Cy4 alkyl, C;-C4 haloalkyl, C;-C4 alkoxy, C;-C4 haloalkoxy, C;-C, alkylthio, C,-C4 alkylsulfinyl, C;-C, alkylsulfonyl, halogen or CN; and pis 0, 1 or 2. . :

11. The method of Claim 10 wherein J is a pyridine optionally substituted with 1 to 3

R7. - CL

12. The method of Claim 11 wherein one R7 is a phenyl optionally substituted with C;-C4 alkyl, C{~C4 haloalkyl, halogen or CN.

13. The method of Claim 11 wherein one R7 is a pyrazole, imidazole, triazole, ‘ pyridine or pyrimidine, each ring optionally substituted with C{-Cy4 alkyl, C1-C4 haloalkyl, i 5 halogen or CN. ) 14. The method of Claim 10 wherein J is a pyrimidine optionally substituted with 1 to 3 R7. : 15. The method of Claim 14 wherein one R7 is a phenyl optionally substituted with C;-C4 alkyl, C-C, haloalkyl, halogen or CN.

16. The method of Claim 14 wherein one R7 is a pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted with C;-C, alkyl, C;-C4 haloalkyl, halogen or CN.

17. The method of Claim 10 wherein J is a pyrazole optionally substituted with 1 to

3R7. :

18. The method of Claim 17 wherein one R7 is a phenyl optionally substituted with C,-C4 alkyl, C-C, haloalkyl, halogen or CN.

19. The method of Claim 17 wherein one R7 is a pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted with C;-Cy4 alkyl, C;-C, haloalkyl, halogen or CN. :

20. The method of Claim 19 wherein R7 is a pyridine optionally substituted with C,-C,4 alkyl, C;-C4 haloalkyl, halogen or CN.

21. The method of Claim 1 comprising a compound of Formula 1 selected from the group consisting of: 3-methyl-N-(1-methylethyl)-2-[[4-(trifluoromethyl)benzoyl Jamino]-benzamide, 2-methyl-N-[2-methyl-6-[[(1 -methylethyl)amino]carbonyl]phenyl]-4- (trifluoromethyl)benzamide, 2-methyl-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-6- (trifluoromethyl)-3-pyridinecarboxamide, 1-ethyl-N-[2-methyl-6-[[(1-methylethyl)amino]carbonylJphenyl]-3- (trifluoromethyl)-1H-pyrazole-5-carboxamide, 1-(2-fluorophenyl)-N-[2-methyl-6- [1 -methylethyl)amino)carbonyl]phenyl]-3- (trifluoromethyl)-1H-pyrazole-5-carboxamide, 1-(3~chloro-2-pyridinyl)-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]3- (trifluoromethyl)-1 H-pyrazole-5-carboxamide, N-[2-chloro-6-[[(1-methylethyl)amino]carbonyl]phenyl]-1-(3-chloro-2-pyridinyl)-3- (trifluoromethyl)-1H-pyrazole-5-carboxamide, : :

3-bromo-1-(2-chlorophenyl)-N-[2-methyl-6-[[(1- methylethyl)amino]carbonyl]phenyl]-1 Z-pyrazole-5-carboxamide, and 3-bromo-N-[2-chloro-6-[[(1-methylethyl)amino]carbonyl] phenyl]-1-(2- chlorophenyl)-1H-pyrazole-5-carboxamide.

22. A compound of Formula 1, its N-oxides and agriculturally suitable salts A J , 1 3 2 No R!

LL . 3 ZZ Rp wherein A and B are independently O or S; each J is independently a phenyl or naphthyl group substituted with 1 to 2 R® and ‘optionally substituted with 1 to 3 RS; : or each J is independently a 5- or 6-membered heteroaromatic ring or an aromatic $-, 9- or 10-membered fused heterobicyclic ring system wherein each ring or ring system is optionally substituted with 1 to 4 R7; nis tod; Rlis Hj or C;-Cg alkyl, C»-Cg alkenyl, C,-Cg alkynyl or C5-Cy cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO,, hydroxy, C1-C4 alkoxy, C,-Cy4 alkylthio, C1-Cy alkylsulfinyl, C;-Cy alkylsulfonyl, C,-C4 alkoxycarbonyl, C;-C, alkylamino, C,-Cg dialkylamino and C3-Cg4 cycloalkylamino; or Ris Cy-Cg alkylcarbonyl, C,-Cg alkoxycarbonyl, C,-Cg alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl or C(=A)J: R2is H, C-Cg alkyl, C,-Cg alkenyl, C,-Cg alkynyl, C3-Cg cycloalkyl, C;-C, alkoxy, C1-C4 alkylamino, C,-Cyg dialkylamino, C3-Cg cycloalkylamino, C,-Cy alkoxycarbonyl or C,-Cg alkylcarbonyl; R3 is H; C;-Cg alkyl, Cy-Cg alkenyl, C,-Cg alkynyl, C5-Cg cycloalkyl, each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO,, hydroxy, C;-C4 alkoxy, C;-C, haloalkoxy, C1-Cy4 alkylthio, Cy-Cy alkylsulfinyl, C;-C4 alkylsulfonyl, C,-Cg alkoxycarbonyl, C5-Cg alkylcarbonyl, C3-Cg trialkylsilyl, or a phenoxy ring optionally substituted with : one to three substituents independently selected from the group consisting of C 1- oo 203 : Amended Sheet — 2003-11-11

C, alkyl, C,-C4 alkenyl, C,-Cy4 alkynyl, C3-Cg cycloalkyl, C;-C4 haloalkyl, Cy- C, haloalkenyl, C,-C,4 haloalkynyl, C3-Cg halocycloalkyl, halogen, CN, NO,, ) C,-C4 alkoxy, C,-C4 haloalkoxy, C;-C, alkylthio, C;-C4 alkylsulfinyl, C;-C4 alkylsulfonyl, C{-C4 alkylamino, C,-Cgq dialkylamino, C3-Cg cycloalkylamino, . 5 C3-C¢ (alkyl)cycloalkylamino, C,-C, alkylcarbonyl, C,-C¢ alkoxycarbonyl, C,- Cg alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl or C3-Cg trialkylsilyl; Cy- C4 alkoxy; C1-Cy4 alkylamino; C,-Cg dialkylamino; C3-Cg cycloalkylamino; C,- Cg alkoxycarbonyl or C»-Cg alkylcarbonyl; or RZ? and R3 can be taken together with the nitrogen to which they are attached to form a ring containing 2 to 6 atoms of carbon and optionally one additional atom of nitrogen, sulfur or oxygen, said ring may be optionally substituted with 1 to 4 substituents selected from the group consisting of C;-C, alkyl, halogen, CN, NO; and C;-C, alkoxy; each R4 is independently H, C;-Cg alkyl, C5-Cg4 alkenyl, C,-Cg alkynyl, C3-Cg cycloalkyl, C1-Cg haloalkyl, C5-Cg4 haloalkenyl, C5-C¢ haloalkynyl, C3-Cg halocycloalkyl, halogen, CN, NO,, hydroxy, C;-C4 alkoxy, C;-C4 haloalkoxy, C;-C, alkylthio, C;-C4 alkylsulfinyl, C;-C, alkylsulfonyl, C;-C4 haloalkylthio, C;-C, haloalkylsulfinyl, C;-C4 haloalkylsulfonyl, C;-C, alkylamino, C,-Cg dialkylamino, C3-Cg cycloalkylamino, or C3-Cg trialkylsilyl; or each R#4 is independently phenyl, benzyl or phenoxy, each optionally substituted with Cy-C4 alkyl, C,-Cy alkenyl, C,-C, alkynyl, C3-Cg cycloalkyl, C;-Cy4 haloalkyl, C,-C4 haloalkenyl, C,-C4 haloalkynyl, C3-Cg halocycloalkyl, halogen, CN, NO,, C4-C4 alkoxy, C1-C4 haloalkoxy, C;-C4 alkylthio, Cy-C4 alkylsulfinyl, C;- C, alkylsulfonyl, C;-C4 alkylamino, C,-Cg dialkylamino, C3-Cg cycloalkylamino, C5-Cg (alkyl)eycloalkylamino, C,-C; alkylearbonyl, C5-Cg alkoxycarbonyl, C5-Cg¢ alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl or Cs- Cg trialkylsilyl; each RS is independently C;-Cg haloalkyl, C,-Cg haloalkenyl, C,-Cg4 haloalkynyl, Cs- Cg halocycloalkyl, C;-Cy4 haloalkoxy, C;-C4 alkylthio, C;-C4 alkylsulfinyl, C,- Cy alkylsulfonyl, C,-C,4 baloalkylthio, C;-C4 haloalkylsulfinyl, C;-C4 haloalkylsulfonyl, CN, NO,, C;-Cy4 alkoxycarbonyl, C{-Cy alkylamino, C,-Cg dialkylamino, C3-Cg4 cycloalkylamino, C,-Cg alkylcarbonyl, Co-Cg alkoxycarbonyl, C,-Cg4 alkylaminocarbonyl, or C3-Cg dialkylaminocarbonyl; or } (R>), attached to adjacent carbon atoms can be taken together as -OCF,0-, -CF,CF,0-, or -OCF,CF,0-; : each RS is independently H, halogen, C;-Cg alkyl, C,-Cg alkenyl, C,-Cg alkynyl, C;- Cg cycloalkyl, C;-C4 alkoxy or C,-C, alkoxycarbonyl; or oo each RS is independently a phenyl, benzyl, phenoxy, 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system, each ring optionally substituted with one to three substituents independently selected from the group consisting of C,-Cy4 alkyl, C,-C4 alkenyl, C,-C, alkynyl, C5-Cy cycloalkyl, C,-C,4 haloalkyl, C,-C4 haloalkenyl, Cy-Cy haloalkynyl, C5-Cg halocycloalkyl, halogen, CN, NO,, C;-Cy4 alkoxy, C;-Cy4 haloalkoxy, C;-Cq : alkylthio, Cy-Cy alkylsulfinyl, C,-C, alkylsulfonyl, C 1-C4 alkylamino, C,-Cg : dialkylamino, C3-Cy cycloalkylamino, C3-Cg (alkyl)cycloalkylamino, Cy-Cy alkylearbonyl, C;-Cg alkoxycarbonyl, C5-Cy allcylaminocarbonyl, C5-Cyg dialkylaminocarbony! or C3-Cg trialkylsilyl; each R7 is independently H, C{-Cg alkyl, C,-Cg alkenyl, C,-Cg alkynyl, C3-Cq cycloalkyl, Cy-Cg haloalkyl, C;-Cg haloalkenyl, C»-Cg haloalkynyl, C3-Cg halocycloalkyl, halogen, CN, CO,H, CONH,, NO,, hydroxy, C,-Cy4 alkoxy, n C1-Cy haloalkoxy, C;-C4 alkylthio, C{-Cy4 alkylsulfinyl, C;-C, alkylsulfonyl,

15 . C4-Cy4 haloalkylthio, C1-C4 haloalkylsulfinyl, C;-C, haloalkylsulfonyl, C;-C4 alkylamino, C,-Cy dialkylamino, C3-Cg4 cycloalkylamino, C;-C alkylcarbonyl, C,-Cg alkoxycarbonyl, C;-Cg alkylaminocarbonyl, C3-Cy dialkylaminocarbonyl, C3-Cg trialkylsilyl; or each R7 is independently a phenyl, benzyl, benzoyl, phenoxy or 5- or 6-membered heteroaromatic ring 8-, 9- or 10-membered fused heterobicyclic ring system, each ring optionally substituted with one to three substituents independently selected from the group consisting of C;-Cy alkyl, C,-C4 alkenyl, Co-Cy4 alkynyl, C3-Cg cycloalkyl, C;-Cy4 haloalkyl, C,-C, haloalkenyl, C,-C,4 haloalkynyl, Cs- Cg halocycloalkyl, halogen, CN, NO,, C;-C, alkoxy, C1-C4 haloalkoxy, C{-Cy4 alkylthio, C,-C4 alkylsulfinyl, C;-C4 alkylsulfonyl, C;-C, alkylamino, C,-Cyq : dialkylamino, C5-Cg cycloalkylamino, C3-Cg (alkyl)cycloalkylamino, Cy-Cy alkylcarbonyl, C,-Cg alkoxycarbonyl, C,-Cg alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl or C3-Cg trialkylsilyl; provided that (i) at least one R* and at least one R7 are other than H; (i1) J is other than an optionally substituted 1,2,3-thiadiazole; (iii) when J is an optionally substituted pyridine and R2 is H, R3 is other than H or CH; (iv) when J is an optionally substituted pyridine, then R7 cannot be CONH,, Cy-Cq alkylaminocarbonyl or C3-Cg dialkylaminocarbonyl; (v) when J is an optionally substituted pyrazole, tetrazole or pyrimidine, then R? and R3 cannot both be hydrogen; (vi) when J is an optionally substituted tetrazole, then R7 is other than an optionally ’ substituted benzyl. ] 205 Amended Sheet — 2003-11-11

23. The compound of Claim 22 wherein J is a phenyl group substituted with 1 to 2 R73 and optionally substituted with 1 to 3 RS.

24. The compound of Claim 23 wherein : A and B are both O; nis 1to?2; Ris H, C;-Cy alkyl, Co-Cy alkenyl, Cp-C, alkynyl, C3-Cg cycloalkyl, Cp-Cs alkylcarbonyl or C,-Cg alkoxycarbonyl; R? is H, C)-Cy alkyl, C5-Cy alkenyl, C5-Cy alkynyl, C3-Cg cycloalkyl, Cy-Cq alkylcarbonyl or C;-Cg4 alkoxycarbonyl; Ris C;-Cg alkyl, Co-Cg alkenyl, C»-Cg alkynyl or C3-Cg cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, C,-C; alkoxy, C;-C; alkylthio, C;-C; alkylsulfinyl and C;-C, alleylsulfonyl; s one of the R* groups is attached to the phenyl ring af the 2-position or 5-position, and said R* is Cy-Cy4 alkyl, C}-C4 haloalkyl, halogen, CN, NO,, C;-C4 alkoxy, C;- C4 haloalkoxy, C;-C, alkylthio, C-Cy alkylsulfinyl, C-Cy4 alkylsulfonyl, C;-Cy4 haloalkylthio, C;-Cy4 haloalkylsulfinyl or C;-C,4 haloalkylsulfonyl; each R3 is independently C,-C, haloalkyl, CN, NO,, C;-C,4 haloalkoxy, Ci-Cy - alkylthio, C;-C4 alkylsulfinyl, C;-Cy4 alkylsulfonyl, C,-C4 haloalkylthio, C;-Cy4 haloalkylsulfinyl, C;-C,4 haloalkylsulfonyl or C5-Cy4 alkoxycarbonyl; or (R3), when attached to adjacent carbon atoms can be taken together as -OCF,0-, -CF,CF,0- or -OCF,CF,0-; and each RS is independently H, halogen, C;-Cy alkyl, C1-C, alkoxy or C,-C4 alkoxycarbonyl, or : each RO is independently a phenyl or a 5- or 6-membered heteroaromatic ring, each ring optionally substituted with C1-C, alkyl, C,-Cy alkenyl, C.-C, alkynyl, Cs- Cg cycloalkyl, C;-Cy4 haloalkyl, C»-C4 haloalkenyl, C,-C,4 haloalkynyl, C5-Cg halocycloalkyl, halogen, CN, NO, C;-Cy alkoxy, C;-C4 haloalkoxy, C1-C,4 alkylthio, C;-Cy4 alkylsulfinyl, C;-C4 alkylsulfonyl, C;-C, alkylamino, C,-Cg dialkylamino, C3-Cg cycloalkylamino, C3-Cg (alkyl)cycloalkylamino, Cy-Cy alkylcarbonyl, C,-Cg alkoxycarbonyl, C,-Cg alkylaminocarbonyl, C5-Cg dialkylaminocarbony! or C5-Cg trialkylsilyl.

25. The compound of Claim 24 wherein ) R! and R? arc both H; R3 is C;-Cy alkyl optionally substituted with halogen, CN, OCHj, S(0)pCHs; each R* is independently H, CHjs, CF3, OCF3, OCHF5, S(0),CF3, S(0)pCHE7, CN or halogen; : 206 . Amended Sheet — 2003-11-11

RRR g each R3 is independently CF3, OCF, OCHF,, S(0),CF3, S(0),CHF,, OCH, CFs, OCF,CHF,, S(0),CH,CF; or S(O),CF, CHF; each RS is independently H, halogen or methyl; or phenyl, pyrazole, imidazole, : triazole, pyridine or pyrimidine, each ring optionally substituted with Ci1-Cy4 alkyl, C1-C4 haloalkyl, halogen or CN; and ‘ pis 0,1 or2. : : 26. The compound of Claim 25 wherein R3 is i-propyl or t-butyl.

27. The compound of Claim 22 wherein J is a 5- or 6-membered heteroaromatic ring optionally substituted with 1 to 4 R7.

28. The compound of Claim 27 wherein Jis a 5- or 6-membered heteroaromatic ring selected from the group consisting of J-1, J-2, J-3, J-4 and J-5, each J optionally substituted with 1to3R7 A o— x X= 5 x= J : A z A, ANS 7 R 1 32 +3 _X Rr” PRN ) Ww? he PA J§ PENG. AY 1-4 1-5 QisO,S orNR7; and W, X,Y and Z are independently N or CR’, provided that in J-4 and J-5 at least one of W,X,YorZisN.

29. The compound of Claim 27 or Claim 28 wherein A and B are O; nis lto2; Rlis H, C}-Cy alleyl, C5-Cy alkenyl, Cy-Cy alkynyl, Cy-Cy alkylearbonyl or C,-Cyg alkoxycarbonyl; : © R%isH, C;-C4 alkyl, Cy-Cy alkenyl, C,-Cy alkynyl, C5-Cg cycloalkyl, Cy-Cy allkylcarbonyl or C,»-Cg alkoxycarbonyl; R3 is H; or C;-Cg alkyl, C5-Cg alkenyl, C,-Cg alkynyl or C3-Cg4 cycloalkyl each optionally substituted with one or more substituents selected from the group oo 207 oo Amended Sheet — 2003-11-11 consisting of halogen, CN, C;-C, alkoxy, C;-C, alkylthio, Cy-C; alkylsulfinyl and C;-C, alkylsulfonyl; one of the R4 groups is attached to the phenyl ring at the 2-position, and said R4 is C- ? C, alkyl, C4-C4 haloalkyl, halogen, CN, NO,, C-C4 alkoxy, C;-C, haloalkoxy, ] 5 C,-Cy4 alkylthio, C;-C4 alkylsulfinyl, C;-C, alkylsulfonyl, C;-C, haloalkylthio, ) C;-C4 haloalkylsulfinyl or C;-C4 haloalkylsulfonyl; and . each R7 is independently H, C1-C, alkyl, C;-C4 haloalkyl, halogen, CN, NO,, C{-C4 haloalkoxy, C;-Cy4 alkylthio, C;-Cy4 alkylsulfinyl, C-Cy alkylsulfonyl, C;-Cy haloalkylthio, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl or C,-C, alkoxycarbonyl; or a phenyl or a 5- or 6-membered heteroaromatic ring, : each ring optionally substituted with C;-C, alkyl, C,-Cy alkenyl, C,-C, alkynyl, C5-Cg cycloalkyl, C1-C, haloalkyl, C»-Cy4 haloalkenyl, C,-Cy4 haloalkynyl, Cs- Cg halocycloalkyl, halogen, CN, NO,, C;-C, alkoxy, C;-C4 haloalkoxy, C;-Cy4 , alkylthio, C;-C, alkylsulfinyl, C;-C, alkylsulfonyl, C;-C, alkylamino, C,-Cg dialkylamino, C3-Cg cycloalkylamino, C3-Cg (alkyl)cycloalkylamino, C,-Cy alkylcarbonyl, C,-Cg alkoxycarbonyl, C,-Cg4 alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl or C3-Cg trialkylsilyl.

30. The compound of Claim 29 wherein J is selected from the group consisting of pyridine, pyrimidine, pyrazole, imidazole, triazole, thiophene, thiazole and oxazole, furan, isothiazole and isoxazole, each optionally substituted with 1 to 3 R7.

31. The compound of Claim 30 wherein 1 is selected from the group consisting of pyridine, pyrimidine, pyrazole, thiophene and thiazole, each optionally substituted with 1 to 3 R7; RI! and R2 are both H; R3 is C;-C alkyl optionally substituted with halogen, CN, OCHjz, S(O),CHj; each R# is independently H, CHj, CF3, OCF3, OCHF», S(O),CF3, S(O),CHF,, CN or halogen; each R7 is independently H, halogen, CHs, CF3, OCHF,, S(0),CF3, S(0),CHF, OCH,CF3, OCF,CHF3, S(0),CH;CF3, S(0)pCF,CHF; or phenyl, pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted with C-C4 alkyl, C1-Cy4 haloalkyl, C,-Cj alkoxy, C;-Cy4 haloalkoxy, C;-Cy4 alkylthio, C,-C4 alkylsulfinyl, C-C4 alkylsulfonyl, halogen or CN; and . pis0, 1or2.

32. The compound of Claim 31 wherein J is a pyridine optionally substituted with 1 to3R7

33. The compound of Claim 32 wherein one R7 is a phenyl optionally substituted with C;-C, alkyl, C;-C4 haloalkyl, halogen or CN. oo 208 oo

34. The compound of Claim 32 wherein one R7 is a pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted with C;-C, alkyl, C;-C, haloalkyl, halogen or CN. > 35. The compound of Claim 31 wherein J is a pyrimidine optionally substituted with 1to3R". } 36. The compound of Claim 35 wherein one R” is a pheny} optionally substituted : with C4-C, alkyl, C;-C4 haloalkyl, halogen or CN.

37. The compound of Claim 35 wherein one R’ is a pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted with C;-C, alkyl, C,-C, haloalkyl, halogen or CN.

38. The compound of Claim 32 wherein J is a pyrazole optionally substituted with 1 to 3 R7.

39. The compound of Claim 38 wherein one R7 is a phenyl optionally substituted with C;-C4 alkyl, C{-C, haloalkyl, halogen or CN.

40. The compound of Claim 38 wherein one R7 is a pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted with C;-Cy4 alkyl, C,-C4 haloalkyl, halogen or CN.

41. The compound of Claim 38 wherein wherein R7 is a pyridine optionally substituted with C;-Cy alkyl, C;-C4 haloalkyl, halogen or CN.

42. The compound of Claim 22 selected from the group consisting of: 3-methyl-N-(1-methylethyl)-2-[[4-(trifluoromethyl)benzoyl]amino]-benzamide, 2-methyl-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-4-

. (trifluoromethyl)benzamide, 2-methyl-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-6- (trifluoromethyl)-3-pyridinecarboxamide, 1-ethyl-N-{2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-3- (trifluoromethyl)-1 H-pyrazole-5-carboxamide, 1-(2-fluorophenyl)-N-[2-methyl-6-[[(1 -methylethyl)amino)carbonyl|phenyl]}-3- (trifluoromethyl)-1 H-pyrazole-5-carboxamide, : 1-(3-chloro-2-pyridinyl)-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]3- (trifluoromethyl)-1/-pyrazole-5 _carboxamide, N-[2-chloro-6-[[(1-methylethyl)amino]carbonyl]phenyl]-1-(3-chloro-2-pyridinyl)-3- (trifluoromethyl)-1 H-pyrazole-5-carboxamide, oo 3-bromo-1-(2-chlorophenyl)-N-[2-methyl-6-[[(1- ) 35 - methylethyl)amino]carbonyl]phenyl]-1 H-pyrazole-5-carboxamide, and 3-bromo-N-[2-chloro-6-[[(1-methylethyl)amino]carbonyl]phenyl]-1-(2- . chlorophenyl)-1H-pyrazole-5-carboxamide.

43. An arthropodicidal composition comprising an arthropodicidally effective amount of a compound of Formula 1 as described in Claim 1 and at least one additional component selected from the group consisting of surfactants, solid diluents and liquid

. diluents.