PatentDe  


Dokumentenidentifikation EP1511385 05.01.2006
EP-Veröffentlichungsnummer 0001511385
Titel INSEKTIZIDE AMIDE MIT STICKSTOFFHALTIGEN KONDENSIERTEN BIZYKLISCHEN RINGSYSTEMEN
Anmelder E.I. du Pont de Nemours and Co., Wilmington, Del., US
Erfinder STEVENSON, Martin, Thomas, Newark, US
Vertreter derzeit kein Vertreter bestellt
DE-Aktenzeichen 60302572
Vertragsstaaten AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IT, LI, LU, MC, NL, PT, RO, SE, SI
Sprache des Dokument EN
EP-Anmeldetag 10.06.2003
EP-Aktenzeichen 037391042
WO-Anmeldetag 10.06.2003
PCT-Aktenzeichen PCT/US03/18610
WO-Veröffentlichungsnummer 0003103398
WO-Veröffentlichungsdatum 18.12.2003
EP-Offenlegungsdatum 09.03.2005
EP date of grant 30.11.2005
Veröffentlichungstag im Patentblatt 05.01.2006
IPC-Hauptklasse A01N 47/38(2006.01)A, F, I, ,  ,  ,   

Beschreibung[en]
FIELD OF THE INVENTION

This invention relates to certain indoline carboxamides and thiamides, their N-oxides, suitable salts and compositions, and a method of their use for controlling invertebrate pests in both agronomic and nonagronomic environments.

BACKGROUND OF THE INVENTION

The control of invertebrate pests is extremely important in achieving high crop efficiency. Damage by invertebrate pests to growing and stored agronomic crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. The control of invertebrate 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.

EP919542 discloses phthalic diamides of Formula i as insecticides

wherein, among others, Z1 and Z2 are O or S; and R1, R2 and R3 are, among others, H, alkyl or substituted alkyl.

WO 96/23783 and US 5514690 disclose indoline carboxamide derivatives as pharmaceutical agents.

SUMMARY OF THE INVENTION

This invention is related to compounds of Formula I and compounds of Formula II including all geometric and stereoisomers, N-oxides and salts thereof:

wherein
each J
is independently a phenyl ring or a 5- or 6-membered heteroaromatic ring, each ring substituted with 1 to 4 R5;
A and B
are independently O or S;
n
is 0, 1, 2 or 3;
R1
is H, C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl or C3-C8 dialkylaminocarbonyl; or
R1
is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C3-C6 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO2, hydroxy, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C2-C4 alkoxycarbonyl, C1-C4 alkylamino, C2-C8 dialkylamino and C3-C6 cycloalkylamino;
R2
is H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C4 alkoxy, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkoxycarbonyl or C2-C6 alkylcarbonyl;
R3
is H; or
R3
is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C3-C6 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO2, hydroxy, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl and C1-C4 alkylsulfonyl; 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 C1-C2 alkyl, halogen, CN, NO2 and C1-C2 alkoxy; and
each R4 and each R5
is independently H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, CO2H, CONH2, NO2, hydroxy, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl, or C3-C6 trialkylsilyl; or
each R4 and each R5
is independently a phenyl, benzyl, phenoxy, or 5- or 6-membered heteroaromatic ring, each ring optionally substituted with one to three substituents independently selected from the group consisting of C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, NO2, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C3-C6 (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl or C3-C6 trialkylsilyl; or
two R5
groups when attached to adjacent carbon atoms can be taken together as -OCF2O-, -CF2CF2O- or -OCF2CF2O-;
M and M1
are each independently CR6R7, NR8, O or S when the bond between M and M1 is a single bond; and are each independently CR6 or N when the bond between M and M1 is an aromatic bond;
each R6 and each R7
is independently H, C1-C4 alkyl, halogen, CN, C1-C4 haloalkyl or C1-C4 alkoxy; and
each R8
is independently H or C1-C4 alkyl.

This invention provides a method for controlling at least one invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of at least one compound selected from the group consisting of a compound of Formula I, an N-oxide or a salt thereof, and a compound of Formula II, an N-oxide or a salt thereof (e.g., as a composition described herein).

Of note is a method for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound of Formula I or a compound of Formula II (e.g., as a composition described herein).

This invention also provides a composition comprising at least one compound selected from the group consisting of a compound of Formula I, an N-oxide or a salt thereof, and a compound of Formula II, an N-oxide or a salt thereof; and at least one other biologically active compound or agent; and provides a method for controlling at least one invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of said composition.

Of note is a composition for controlling an invertebrate pest comprising (1) at least one compound selected from the group consisting of compounds of Formula I and compounds of Formula II, and (2) at least one additional compound or agent for controlling invertebrate pests; and provides a method for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment a biologically effective amount of said composition.

This invention also provides a compound of Formula II, an N-oxide or a salt thereof; a composition which comprises at least one compound of Formula II, an N-oxide or salt thereof; and at least one additional component selected from the group consisting of a surfactant, a solid diluent, a liquid diluent and an other biologically active compound or agent; and a method for controlling at least one invertebrate pest which comprises contacting the invertebrate pest or its environment with a biologically effective amount of said compound(s) or with a biologically effective amount of said composition.

Of note are compounds of Formula II: compositions for controlling an invertebrate pest which comprise at least one compound of Formula II and at least one additional component selected from the group consisting of surfactants, solid diluents, liquid diluents diluents and other biologically active compounds and agents; and methods for controlling an invertebrate pest which comprise contacting the invertebrate pest or its environment a biologically effective amount of said compounds or said compositions.

Of note are compounds of Formula Ic

wherein
M and M1
are each independently CR6R7, NR8, O or S when the bond between M and M1 is a single bond, provided that M and M1 are not both CR6R7; and are each independently CR6 or N when the bond between M and M1 is an aromatic bond; and
A, B, J,
R1 through R4, R6 through R8 and n are defined as above.

This invention also provides compounds of Formula Id

wherein
each R4 and each R5
is independently H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, CO2H, CONH2, NO2, hydroxy, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl, or C3-C6 trialkylsilyl; or
each R5
is independently a phenyl, benzyl, phenoxy, or 5- or 6-membered heteroaromatic ring, each ring optionally substituted with one to three substituents independently selected from the group consisting of C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, NO2, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C3-C6 (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl or C3-C6 trialkylsilyl; or
two R5
groups when attached to adjacent carbon atoms can be taken together as -OCF2O-, -CF2CF2O- or -OCF2CF2O-; and
A, B, J,
R1 through R3, R6 through R8 and n are defined as above.

This invention also provides a composition which comprises at least one compound of Formula Id, an N-oxide or a salt thereof; and at least one additional component selected from the group consisting of a surfactant, a solid diluent, a liquid diluent and an other biologically active compound or agent; and a method for controlling at least one invertebrate pest which comprises contacting the invertebrate pest or its environment with a biologically effective amount of said compound(s) or with a biologically effective amount of said composition.

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. "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. "Alkylthio" includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers. "Alkylsulfinyl" includes both enantiomers of an alkylsulfinyl group. Examples of "alkylsulfinyl" include CH3S(O), CH3CH2S(O), CH3CH2CH2S(O), (CH3)2CHS(O) and the different butylsulfinyl, pentylsulfinyl and hexylsulfinyl isomers. Examples of "alkylsulfonyl" include CH3S(O)2, CH3CH2S(O)2, CH3CH2CH2S(O)2, (CH3)2CHS(O)2 and the different butylsulfonyl, pentylsulfonyl and hexylsulfonyl isomers. "Alkylamino" includes branched or straight-chain alkylamino moieties such as methylamino, ethylamino, and the different propylamino, butylamino, pentylamino and hexylamino isomers. Examples of "alkylcarbonyl" include C(O)CH3, C(O)CH2CH2CH3 and C(O)CH(CH3)2. Examples of "alkoxycarbonyl" include CH3OC(=O), CH3CH2OC(=O), CH3CH2CH2OC(=O), (CH3)2CHOC(=O) and the different butoxy- or pentoxycarbonyl isomers. Examples of "alkylaminocarbonyl" include CH3NHC(=O), CH3CH2NHC(=O), CH3CH2CH2NHC(=O), (CH3)2CHNHC(=O) and the different butylamino- or pentylaminocarbonyl isomers. The term "dialkylamino" includes amino functions substituted with two alkyl groups that may be the same or different. "Dialkylaminocarbonyl" is defined analogously, and examples include (CH3)2NC(=O) and CH3CH2NCH3C(=O).

The term "cycloalkyl", used either alone or in compound words such as "cycloalkylamino" or "halocycloalkyl" includes, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

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 Hückel 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 "halogen", either alone or in compound words such as "haloalkyl", includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as "haloalkyl", said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of "haloalkyl" include F3C, ClCH2, CF3CH2 and CF3CCl2. The terms "haloalkenyl", "haloalkynyl", "haloalkoxy", and the like, are defined analogously to the term "haloalkyl". Examples of "haloalkenyl" include (Cl)2C=CHCH2 and CF3CH2CH=CHCH2. Examples of "haloalkynyl" include HC≡CCHCl, CF3C≡C, CCl3C≡C and FCH2C≡CCH2. Examples of "haloalkoxy" include CF3O, CCl3CH2O, HCF2CH2CH2O and CF3CH2O. Examples of "haloalkylthio" include CCl3S, CF3S, CCl3CH2S and ClCH2CH2CH2S. Examples of "haloalkylsulfinyl" include CF3S(O), CCl3S(O), CF3CH2S(O) and CF3CF2S(O). Examples of "haloalkylsulfonyl" include CF3S(O)2, CCl3S(O)2, CF3CH2S(O)2 and CF3CF2S(O)2.

The combination of a broken line and an unbroken line between M and M1 as shown in Formula I and Formula II designates that the bond between M and M1 can be either a single bond or an aromatic bond. When the bond between M and M1 is an aromatic bond then M, M 1 and the bond between them form a portion of an aromatic ring. For example, when the bond between M and M1 is a single bond and M and M1 are both CR6R7, then M and M1 are both within an indoline ring system; and when the bond between M and M1 is an aromatic bond and M and M1 are both CR6, then M and M1 are both within an indole ring system.

The total number of carbon atoms in a substituent group is indicated by the "Ci-Cj" prefix where i and j are numbers from 1 to 8. For example, C1-C3 alkylsulfonyl designates methylsulfonyl through propylsulfonyl; C2 alkoxyalkyl designates CH3OCH2; C3 alkoxyalkyl designates, for example, CH3CH(OCH3), CH3OCH2CH2 or CH3CH2OCH2; 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 CH3CH2CH2OCH2 and CH3CH2OCH2CH2. In the above recitations, when a compound of Formula 1 contains a heteroaromatic 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. When the number of optional substituents on a group is 0, for example when n is 0, then it is recognized that this is equivalent to said group being unsubstituted. When a bond is depicted as floating, the substituent may be attached to any of the available carbons on the ring by replacement of hydrogen. When R2 and R3 are taken together with the nitrogen to which they are attached to form a ring, said ring can be optionally substituted on any available carbon or optionally nitrogen in said ring.

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. The compounds of the invention can be present as a mixture of stereoisomers, individual stereoisomers, or as an optically active form.

The present invention involves compounds selected from Formula I or Formula II, N-oxides and 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 oxidation of heterocycles and tertiary amines with peroxy acids such as peracetic andm-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides such ast-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethydioxirane. 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 18-19, 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. In the compositions and methods of this invention, the salts of the compounds of the invention are preferably suitable for the agronomic and/or nonagronomic uses described herein.

As noted above, this invention includes a method for controlling at least one invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of at least one of a compound selected from the group consisting a compound of Formula I, an N-oxide or a salt thereof, and a compound of Formula II, an N-oxide or salt thereof. Preferred methods for reasons including greater control of invertebrate pests and/or ease of compound synthesis are:

  • Preferred 1. The method comprising applying a biologically effective amount of a compound of Formula I wherein
    A and B
    are both O;
    R1
    is H, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C2-C6 alkylcarbonyl or C2-C6 alkoxycarbonyl; and
    n
    is 0, 1 or 2.
  • Preferred 2. The method comprising applying a biologically effective amount of a compound of Formula II wherein
    A and B
    are both O;
    R1
    is H, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C2-C6 alkylcarbonyl or C2-C6 alkoxycarbonyl; and
    n
    is 0, 1 or 2.
  • Preferred 3. The method of Preferred 1 or Preferred 2 comprising applying a biologically effective amount of a compound of Formula I or a compound of Formula II wherein
    J
    is a phenyl ring or a 5- or 6-membered heteroaromatic ring selected from the group consisting of J-1, J-2, J-3 and J-4
    Q
    is O, S or NR5;
    W, X, Y and Z
    are independently N or CR5, provided that in J-3 and J-4 at least one of the group consisting of W, X, Y and Z is N;
    R2
    is H, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C2-C6 alkylcarbonyl or C2-C6 alkoxycarbonyl;
    R3
    is H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C3-C6 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, C1-C2 alkoxy, C1-C2 alkylthio, C1-C2 alkylsulfinyl and C1-C2 alkylsulfonyl;
    each R4
    is independently C1-C4 alkyl, C1-C4 haloalkyl, halogen, CN, NO2, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl or C1-C4 haloalkylsulfonyl;
    each R5
    is independently H, C1-C4 alkyl, C1-C6 haloalkyl, halogen, CN, NO2, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl or C2-C4 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl; or
    each R5
    is independently a phenyl, benzyl or a 5- or 6-membered heteroaromatic ring, each ring optionally substituted with C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, NO2, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C3-C6 (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl or C3-C6 trialkylsilyl; or
    two R5
    groups when attached to adjacent carbon atoms can be taken together as -OCF2O-, -CF2CF2O- or -OCF2CF2O-.
  • Preferred 4. The method of Preferred 3 comprising applying a biologically effective amount of a compound of Formula I wherein
    R1
    is H or C1-C4 alkyl;
    R2
    is H or C1-C4 alkyl;
    R3
    is H, C1-C4 alkyl optionally substituted with halogen, CN, OCH3, or S(O)pCH3;
    each R5
    is independently H, C1-C4 alkyl, C1-C4 haloalkyl, halogen, CN, NO2, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, C2-C4 alkoxycarbonyl or C3-C8 dialkylaminocarbonyl; or a phenyl, benzyl, or a 5- or 6-membered heteroaromatic ring, each ring optionally substituted with halogen, CN, NO2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy;

    provided that at least one R5 is other than H and is attached to J at the positionortho to the N(R1)C(=B) moiety; and
    p
    is 0, 1 or 2.
  • Preferred 5. The method of Preferred 4 comprising applying a biologically effective amount of a compound of Formula I wherein
    J
    is a substituted phenyl, a substituted pyrazole, a substituted pyrrole, a substituted pyridine or a substituted pyrimidine.
  • Preferred 6. The method of Preferred 5 comprising applying a biologically effective amount of a compound of Formula I wherein
    R1 and R2
    are each H.
  • Preferred 7. The method of Preferred 3 comprising applying a biologically effective amount of a compound of Formula II wherein
    R2
    is H;
    R3
    is C1-C4 alkyl; and
    at least one R5
    is other than H and is attached to J at the position ortho to the N(R1)C(=B) moiety.

As noted above, this invention also provides compounds of Formula Id. Preferred compounds for ease of synthesis and/or greater control of invertebrate pests are:

  • Preferred 8. Compounds of Formula Id wherein
    A and B
    are both O;
    R1
    is H, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C2-C6 alkylcarbonyl or C2-C6 alkoxycarbonyl;
    n
    is 0, 1 or 2.
  • Preferred 9. Compounds of Preferred 8 wherein
    J
    is a phenyl ring or a 5- or 6-membered heteroaromatic ring selected from the group consisting of J-1, J-2, J-3 and J-4
    Q
    is O, S or NR5;
    W, X, Y and Z
    are independently N or CR5, provided that in J-3 and J-4 at least one of the group consisting of W, X, Y and Z is N;
    R2
    is H, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C2-C6 alkylcarbonyl or C2-C6 alkoxycarbonyl;
    R3
    is H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C3-C6 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, C1-C2 alkoxy, C1-C2 alkylthio, C1-C2 alkylsulfinyl and C1-C2 alkylsulfonyl;
    each R4
    is independently C1-C4 alkyl, C1-C4 haloalkyl, halogen, CN, NO2, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl or C1-C4 haloalkylsulfonyl;
    each R5
    is independently H, C1-C4 alkyl, C1-C6 haloalkyl, halogen, CN, NO2, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl or C2-C4 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl; or
    each R5
    is independently a phenyl, benzyl or a 5- or 6-membered heteroaromatic ring, each ring optionally substituted with C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, NO2, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C3-C6 (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl or C3-C6 trialkylsilyl; or
    two R5
    groups when attached to adjacent carbon atoms can be taken together as -OCF2O-, -CF2CF2O- or -OCF2CF2O-.
  • Preferred 10. Compounds of Preferred 9 wherein
    R1
    is H or C1-C4 alkyl;
    R2
    is H or C1-C4 alkyl;
    R3
    is H, C1-C4 alkyl optionally substituted with halogen, CN, OCH3, or S(O)pCH3;
    each R5
    is independently H, C1-C4 alkyl, C1-C4 haloalkyl, halogen, CN, NO2, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, C2-C4 alkoxycarbonyl or C3-C8 dialkylaminocarbonyl; or a phenyl, benzyl, or a 5- or 6-membered heteroaromatic ring, each ring optionally substituted with halogen, CN, NO2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy;

    provided that at least one R5 is other than H and is attached to J at the positionortho to the N(R1)C(=B) moiety; and
    p
    is 0,1 or 2.
  • Preferred 11. Compounds of Preferred 10 wherein
    J
    is a substituted phenyl, a substituted pyrazole, a substituted pyrrole, a substituted pyridine or a substituted pyrimidine.
  • Preferred 12. Compounds of Preferred 11 wherein R1 and R2 are each H.

Of note are compounds of Formula Ic. Preferred compounds of Formula Ic for ease of synthesis and/or greater control of invertebrate pests are:

  • Preferred 8a. Compounds of Formula Ic wherein
    A and B
    are both O;
    R1
    is H, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C2-C6 alkylcarbonyl or C2-C6 alkoxycarbonyl; and
    n
    is 0, 1 or 2.
  • Preferred 9a. Compounds of Preferred 8a wherein
    J
    is a phenyl ring or a 5- or 6-membered heteroaromatic ring selected from the group consisting of J-1, J-2, J-3 and J-4
    Q
    is O, S or NR5;
    W, X, Y and Z
    are independently N or CR5, provided that in J-3 and J-4 at least one of the group consisting of W, X, Y and Z is N;
    R2
    is H, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C2-C6 alkylcarbonyl or C2-C6 alkoxycarbonyl;
    R3
    is H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C3-C6 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, C1-C2 alkoxy, C1-C2 alkylthio, C1-C2 alkylsulfinyl and C1-C2 alkylsulfonyl;
    each R4
    is independently C1-C4 alkyl, C1-C4 haloalkyl, halogen, CN, NO2, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl or C1-C4 haloalkylsulfonyl;
    each R5
    is independently H, C1-C4 alkyl, C1-C6 haloalkyl, halogen, CN, NO2, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl or C2-C4 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl; or
    each R5
    is independently a phenyl, benzyl or a 5- or 6-membered heteroaromatic ring, each ring optionally substituted with C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, NO2, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C3-C6 (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl or C3-C6 trialkylsilyl; or
    two R5
    groups when attached to adjacent carbon atoms can be taken together as -OCF2O-, -CF2CF2O- or -OCF2CF2O-.
  • Preferred 10a. Compounds of Preferred 9a wherein
    R1
    is H or C1-C4 alkyl;
    R2
    is H or C1-C4 alkyl;
    R3
    is H, C1-C4 alkyl optionally substituted with halogen, CN, OCH3, or S(O)pCH3;
    each R5
    is independently H, C1-C4 alkyl, C1-C4 haloalkyl, halogen, CN, NO2, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, C2-C4 alkoxycarbonyl or C3-C8 dialkylaminocarbonyl; or a phenyl, benzyl, or a 5- or 6-membered heteroaromatic ring, each ring optionally substituted with halogen, CN, NO2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy;

    provided that at least one R5 is other than H and is attached to J at the positionortho to the N(R1)C(=B) moiety; and
    p
    is 0, 1 or 2.
  • Preferred 11a. Compounds of Preferred 10a wherein
    J
    is a substituted phenyl, a substituted pyrazole, a substituted pyrrole, a substituted pyridine or a substituted pyrimidine.
  • Preferred 12a. Compounds of Preferred 11a wherein R1 and R2 are each H.

As noted above, this invention also provides compounds of Formula II. Preferred compounds for ease of synthesis and/or greater control of invertebrate pests are:

  • Preferred 13. Compounds of Formula II wherein
    A and B
    are both O;
    R1
    is H, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C2-C6 alkylcarbonyl or C2-C6 alkoxycarbonyl; and
    n
    is 0, 1 or 2.
  • Preferred 14. Compounds of Preferred 13 wherein
    J
    is a phenyl ring or a 5- or 6-membered heteroaromatic ring selected from the group consisting of J-1, J-2, J-3 and J-4
    Q
    ios O, S or NR5;
    W, X, Y and Z
    are independently N or CR5, provided that in J-3 and J-4 at least one of the group consisting of W, X, Y and Z is N;
    R2
    is H, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C2-C6 alkylcarbonyl or C2-C6 alkoxycarbonyl;
    R3
    is H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C3-C6 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, C1-C2 alkoxy, C1-C2 alkylthio, C1-C2 alkylsulfinyl and C1-C2 alkylsulfonyl;
    each R4
    is independently C1-C4 alkyl, C1-C4 haloalkyl, halogen, CN, NO2, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl or C1-C4 haloalkylsulfonyl;
    each R5
    is independently H, C1-C4 alkyl, C1-C6 haloalkyl, halogen, CN, NO2, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl or C2-C4 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl; or
    each R5
    is independently a phenyl, benzyl or a 5- or 6-membered heteroaromatic ring, each ring optionally substituted with C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, NO2, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C3-C6 (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl or C3-C6 trialkylsilyl; or
    two R5
    groups when attached to adjacent carbon atoms can be taken together as -OCF2O-, -CF2CF2O- or -OCF2CF2O-.
  • Preferred 15. Compounds of Formula II of Preferred 14 wherein
    R2
    is H;
    R3
    is C1-C4 alkyl; and
    at least one R5 is other than H and is attached to J at the position ortho to the N(R1)C(=B) moiety.

This invention also provides a composition comprising at least one compound selected from the group consisting of a compound of Formula I, an N-oxide or a salt thereof, and a compound of Formula II, an N-oxide or a salt thereof; and at least one other biologically active compound or agent; and also provides a method for controlling at least one invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of said composition. Preferred compositions include compositions wherein the at least one compound of Formula I, an N-oxide or a salt thereof and/or Formula II, an N-oxide or a salt thereof is selected from the compounds in Preferred 1 through 7. Also preferred is a composition further comprising an additional component selected from the group consisting of a surfactant, a solid diluent, and a liquid diluent.

Of note are compositions for controlling an invertebrate pest comprising (1) at least one compound selected from the group consisting of compounds of Formula I and compounds of Formula II, and (2) at least one additional compound or agent for controlling invertebrate pests; and also provides a method for controlling an invertebrate pest comprising the invertebrate pest or its environment a biologically effective amount of said composition. Preferred compositions include compositions wherein component (1) is selected from compounds(s) of Formula I and/or Formula II as preferred for the preferred method in Preferred 1 through 7.

This invention also provides a composition comprising at least one compound of Formula II, an N-oxide or a salt thereof; and at least one additional component selected from the group consisting of a surfactant, a solid diluent, a liquid diluent and an other biologically active compound or agent; and also provides a method for controlling at least one invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of said compound(s) of Formula II, its N-oxides and salts thereof or with a biologically effective amount of said composition. Preferred compositions and methods include compositions and methods wherein the at least one compound of Formula II, an N-oxides or a salt thereof, is selected from the compounds in Preferred 13 through 15.

Of note is a composition for controlling an invertebrate pest comprising at least one compound of Formula II and at least one additional component selected from the group consisting of surfactants, solid diluents, liquid diluents and other biologically active compounds and agents; and also provides a method for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment a biologically effective amount of said composition. Preferred compositions include compositions wherein the compound(s) of Formula II, are selected from the compounds preferred in Preferred 13 through 15.

This invention also provides a composition comprising at least one compound of Formula Id, an N-oxide or a salt thereof; and at least one additional component selected from the group consisting of a surfactant, a solid diluent, a liquid diluent and an other biologically active compound or agent; and also provides a method for controlling at least one invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of said compound(s) or with a biologically effective amount of said composition. Preferred compositions and methods include compositions and methods

wherein the at least one compound of Formula Id, a N-oxide or a salt thereof, is selected from the compounds in Preferred 8 through 12.

Of note is a composition for controlling an invertebrate pest comprising at least one compound of Formula Ic and at least one additional component selected from the group consisting of surfactants, solid diluents, liquid diluents and other biologically active compounds or agents; and also provides a method for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment a biologically effective amount of said composition. Preferred compositions include compositions wherein the compound(s) of Formula Ic are selected from the compounds preferred in Preferred 8a through 12a.

As noted above, each J is independently a phenyl ring or a 5- or 6-membered heteroaromatic ring wherein each ring is substituted with 1 to 4 R5. An example of phenyl substituted with 1 to 4 R5 is the ring illustrated as U-1 in Exhibit 1, wherein Rv is R5 and r is an integer from 1 to 4. Examples of 5- or 6-membered heteroaromatic rings optionally substituted with 1 to 4 R5 include the rings U-2 through U-53 illustrated in Exhibit 1 wherein Rv is R5 and r is an integer from 1 to 4. Note that J-1 through J-4 above also denote 5- or 6-membered heteroaromatic rings. Note that U-2 through U-20 are examples of J-1, U-21 through U-35 and U-40 are examples of J-2, U-41 through U-48 are examples of J-3 and U-49 through U-53 are examples of J-4.

Note that when Rv is H when attached to an atom, this is the same as if said atom is unsubstituted. The nitrogen atoms that require substitution to fill their valence are substituted with H or Rv. Note that some U groups can only be substituted with less than 4 Rv groups (e.g. U-14, U-15, U-18 through U-21 and U-32 through U-34 can only be substituted with one Rv). Note that when the attachment point between (Rv)r and the U group is illustrated as floating, (Rv)r can be attached to any available carbon atom of the U group.

The compounds of Formula I and Formula II can be prepared by one or more of the following methods and variations as described in Schemes 1-11. The definitions of R1, R2, R3, R4, A, B, M, M 1 and n in the compounds described in the Schemes below are as defined above in the Summary of the Invention or their subsets unless otherwise indicated. Compounds of Formulae Ia-d are subsets of the compounds of Formula I.

As illustrated in Scheme 1, compounds of Formula I can be prepared by coupling compounds of Formula 1 with either iso(thio)cyanates of Formula 2a or (thio)carbamyl chlorides of Formula 2b. In the case of the (thio)carbamyl chloride reaction the presence of an acid acceptor is advantageous. Tertiary amines and alkali (such as lithium, sodium or potassium) carbonates and acetates are preferred as acid acceptors. Triethylamine is especially preferred. The reaction can be carried out at temperatures in the range of -30 to 120 °C. The reaction can be carried out in a variety of aprotic solvents which do not react with iso(thio)cyanates and (thio)carbamyl chlorides. Preferred solvents include, for example but not limited to, dichloromethane, toluene, ether, ethyl acetate and chloroform. General synthetic methods to prepare iso(thio)cyanates and (thio)carbamyl chlorides from their amine precursors can be found in WO 01/56962, EP 1006102 and EP 919542. The said amine precursors can be prepared by methods disclosed in WO 02/32856.

Compounds of Formula 1 can be synthesized by removal of the BOC (i.e. t-BuOOC) group found in compounds of Formula 3 as shown in Scheme 2. Reaction of a compound of Formula 3 with an acid in the presence of a suitable solvent produces a compound of Formula 1. A wide variety of acids can be used for the deprotection, including, for example but not limited to, hydrochloric acid, hydrobromic acid, triflic acid, trifluoracetic acid, acetic acid, and methanesulfonic acid. Suitable solvents include both aqueous and organic solvents. A preferred combination of acid and solvent is trifluoroacetic acid in dichloromethane.

Compounds of Formula 3 can be prepared by lithiation of compounds of Formula 4 followed by quenching with either iso(thio)cyanates of Formula 5a or (thio)carbamyl chlorides of Formula 5b as shown in Scheme 3 (using iso(thio)cyanates of Formula 5a, R3 in the product of Formula 3 is H). The lithiation can be carried out with an alkyl lithium reagent or a lithium dialkylamide reagent at temperatures in the range of -100 to 0 °C. The preferred conditions involve the use of t-butyllithium in ether at -78 °C. After addition of iso(thio)cyanates or (thio)carbamyl chlorides the reaction is allowed to warm to room temperature or is heated to temperatures between 20 and 120 °C. For a leading reference to the lithiation of indolines (M and M1 are independently CR6R7 and the bond between M and M1 is a single bond) see, Iwao and Kuraishi, Heterocycles,1992, 34, 1031-1038. Iso(thio)cyanates of Formula 5a and (thio)carbamyl chlorides of Formula 5b are commercially available, well known in the chemical literature or can be made by general methods known in the chemical literature.

As shown in Scheme 4, a compound of Formula 4 can be prepared by reaction of a heterocycle of Formula 6 with di-tert-butyl dicarbonate. The reaction can be carried out at temperatures in the range of -70 to 120 °C in the presence of an acid acceptor. Tertiary amines and alkali (such as lithium, sodium or potassium) carbonates, hydroxides and acetates are preferred as acid acceptors. Triethylamine is especially preferred. The reaction is generally conducted in a solvent, such as dichloromethane, toluene, ether, ethyl acetate and chloroform.

Compounds of Formula II can be prepared by reaction of compounds of Formula 7 with either iso(thio)cyanates of Formula 5a or (thio)carbamyl chlorides of Formula 5b as shown in Scheme 5. In the case of the (thio)carbamyl chloride reaction, the presence of an acid acceptor is advantageous. Tertiary amines and alkali (such as lithium, sodium or potassium) carbonates and acetates are preferred as acid acceptors. Triethylamine is especially preferred. The reaction can be carried out at temperatures in the range of -30 to 120 °C. The reaction can be carried out in a variety of aprotic solvents which do not react with iso(thio)cyanates and (thio)carbamyl chlorides. Preferred solvents include, for example, dichloromethane, toluene, ether, ethyl acetate and chloroform.

Compounds of Formula 7 can be prepared by removal the BOC (i.e. t-BuOOC) group found in compounds of Formula 8 as shown in Scheme 6. The reaction conditions for this deprotection are already described for the conversion of the compounds of Formula 3 to the compounds of Formula 1 in Scheme 2.

Compounds of Formula 8 can be prepared by lithiation of compounds of Formula 4 followed by quenching with either iso(thio)cyanates of Formula 2a or (thio)carbamyl chlorides of Formula 2b as shown in Scheme 7. The reaction conditions for this conversion are already described for the conversion of the compounds of Formula 4 to the compounds of Formula 3 in Scheme 3.

As shown in Scheme 8, alkylation of a compound of Formula 3a with an alkylating agent of Formula 9 in the presence of a base will provide a compound of Formula 3b wherein R3 is other than H. Compounds of Formula 3a are a subset of compounds of Formula 3 wherein R3 is H. Compounds of Formula 3b are also a subset of compounds of Formula 3 wherein R3 is other than H. In the alkylating agent of Formula 9, X is a leaving group such as halogen (e.g., Br, I), OS(O)2CH3 (methanesulfonate), OS(O)2CF3, OS(O)2Ph-p-CH3 (p-toluenesulfonate), and the like. Examples of suitable bases include alkali (such as lithium, sodium or potassium) metal hydroxides, carbonates, hydrides and alkoxides. The reaction is generally conducted in a suitable solvent such as tetrahydrofuran, dioxane, dimethylsulfoxide and N,N-dimethylacetamide. Other examples of suitable solvents, particularly useful when alkali alkoxides are used as bases, include alcohols such as methanol and ethanol. Preferred conditions involve the use of sodium hydride as a base andN,N-dimethylformamide as a solvent.

As an alternative method to that illustrated in Scheme 2, compounds of Formula 1 can also be prepared by amide formation of compounds of Formula 10 in the presence of an organic dehydrating reagent outlined in Scheme 9. This involves direct dehydrative coupling of a carboxylic acid of Formula 10 with an amine of Formula 11. The dehydrating reagent can be, for example, 1,3-dicyclohexylcarbodiimide (DCC), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDC), carbonyl diimidazole, 2-chloro-N-methylpyridinium iodide (Mukaiyama's reagent), benzotriazol-1-yloxy-tris(dimethylamino)-phosphonium hexafluorophosphate (BOP) and bis(2-oxo-3-oxazolidinyl)phosphinic chloride (BOP chloride). Various polymer-bound versions of these reagents (e.g., polystyrene-supported DCC) can be used. The amide formation is generally conducted in the presence of a base such as triethylamine and diisopropylethylamine. The preferred conditions involve the use of BOP chloride as a dehydrating reagent and triethylamine as a base in acetonitrile at temperatures in the range of 0 to 120 °C. This reaction is well known in the art, and a multitude of conditions and methods can be utilized. Benzotriazole carboxylic acids (compounds of Formula 10 wherein M and M 1 are both N and the bond between them is an aromatic bond) are known in the art (see Japanese Kokai 11171872; Can. J. Chem. 1977, 55, 1653-1657; and Arch. Pharm. (Weinheim, Ger.), 1989, 322, 457-459). Benzimidazole carboxylic acids (compounds of Formula 10 wherein M is N and M1 is CR6 and the bond between them is an aromatic bond) are also known in the art (see Can. J. Chem. 1977, 55, 1653-1657; J. Med. Chem. 1992, 35, 4595-601; Bioorg. Med. Chem. Lett. 1996, 6, 1195-1198; and J.Med. Chem. 1999, 42, 5020-5028). Indazole carboxylic acids (compounds of Formula 10 wherein M is CR6 and M1 is N and the bond between them is an aromatic bond) are also known in the art (see J. Org. Chem. 1980, 45, 3072-7; and Heterocycles 1997, 45, 1833-1838). Indole carboxylic acids (compounds of Formula 10 wherein M and M1 are independently CR6 and the bond between them is an aromatic bond) are also known in the art (see J. Med. Chem. 1996, 39, 4692-4703).

The carboxylic acids of Formula 10a can be prepared by the hydrolysis of thioesters of Formula 12 as shown in Scheme 10. Compounds of Formula 10a is a subset of compounds of Formula 10 where in M and M1 are independently CR6R7 and the bond between them is a single bond. This hydrolysis can be carried out in C1-C4 alcohols (such as methanol and ethanol) with alkali (such as lithium, sodium and potassium) metal hydroxides. The preferred reaction conditions include the use of potassium or sodium hydroxide as a base and methanol or ethanol as a solvent at temperatures in the range of 20 to 120 °C. Compounds of Formula 12 are known in the art and can be prepared by the Sugasawa reaction (Sugasawa et. al. Synthetic Communications, 1990, 20, 71-84).

Indolines of Formula Ia can be oxidized to indoles of Formula Ib as depicted in Scheme 11. Oxidation can be accomplished by using reagents such as 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ), chloranil or manganese dioxide. Oxidations of indolines to indoles are generally well known in the art. For leading references see Tetrahedron Lett.,2001, 42(41), 7277-7280; and Tetrahedron Lett., 2000, 41(35), 6721-6724.

It is recognized that some reagents and reaction conditions described above for preparing compounds of Formula I and Formula II may not be compatible with certain functional groups 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 it is 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 I and II. 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 sequence presented to prepare the compounds of Formula I and II.

One skilled in the art will also recognize that compounds of Formula I and II 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 Examples are, therefore, to be construed as merely illustrative, and not limiting of the disclosure in any way whatsoever. 1H NMR spectra are reported in ppm downfield from tetramethylsilane: s is singlet, d is doublet, t is triplet, q is quartet, m is multiplet, dd is doublet of doublets, dt is doublet of triplets, br s is broad singlet. m. p. is melting point.

EXAMPLE 1 Preparation of 2,3-dihydro-N7-methyl-N1-[2-methyl-4-(trifluoromethyl)phenyl]-1H-indole-1,7-dicarboxamide Step A: Preparation of 2,3-dihydro-1H-indole-7-carboxylic acid

To a solution of S-methyl 2,3-dihydro-1H-indole-7-carbothioate (Synthetic Communications, 1990, 20, 71-84, 26.88 g) in ethanol (500 mL) was added sodium hydroxide (50% aqueous solution, 50 mL) and the mixture was heated at reflux for 4 hours. Most of the ethanol was removed under reduced pressure. The residue was partitioned between water (150 mL) and dichloromethane (100 mL). The aqueous layer was acidified to pH 3 using concentrated hydrochloric acid, whereupon a solid precipitated. The solid was isolated by filtration and allowed to air dry for 2 hours. The dried solid was dissolved in 300 mL of ethyl acetate and dried over magnesium sulfate. The drying agent was removed by filtration and the filtrate was evaporated under reduced pressure to give the title compound (13.7 g) as a solid.

1H NMR (CDCl3) δ 3.08 (2H), 3.75 (2H), 6.59 (1H), 7.20 (1H), 7.61 (1H).

Step B: Preparation of 2,3-dihydro-N-methyl-1H-indole-7-carboxamide

To a solution of 2,3-dihydro-1H-indole-7-carboxylic acid (i.e. the product from step A) (1.0 g, 6.1 mmol) in acetonitrile (30 ml) was added sequentially methylamine (Aldrich, 2M in tetrahydrofuran, 6.13 mL), bis(2-oxo-3-oxazolidinyl)phosphinic chloride (i.e. BOP chloride, Aldrich, 1.56 g, 6.1 mmol), and triethylamine (1.71 ml, 12.3 mmol). The reaction mixture was allowed to stir at 25 °C for 48 hours. The mixture was partitioned between ethyl acetate (100 mL) and water (100 mL). The organic layer was washed with saturated aqueous sodium bicarbonate (50 mL), dried over magnesium sulfate, filtered and concentrated under reduced pressure to give the title compound.

1H NMR (CDCl3) δ 2.95 (3H), 3.02 (2H), 3.69 (2H), 6.21 (1H), 6.3 1 (1H), 6.61 (1H), 7.1 (2H).

Step C: Preparation of 2,3-dihydro-N7-methyl-N1-[2-methyl-4-(trifluoromethyl)phenyl]-1H-indole-1,7-dicarboxamide

To a solution of 2,3-dihydro-N-methyl-1H-indole-7-carboxamide (i.e. the product from Step B) (300 mg) in dichloromethane was added 2-methyl-4-trifluoromethylphenyl isocyanate (0.4 g). After 3 hours the solvent was evaporated under reduced pressure. The residue was triturated with ether, filtered and washed with more ether to provide the title compound (200 mg), a compound of this invention, as a solid melting at 198 - 200 °C.

1H NMR (CDCl3) δ 2.31 (3H), 2.6 (3H), 3.11 (2H), 4.12 (2H), 6.97 (1H), 7.55 (2H), 8.55 (1H).

EXAMPLE 2 Preparation of 2,3-dihydro-N1-(1-methylethyl)-N7-[2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-1H-indole-1,7-dicarboxamide Step A: Preparation of 1,1-dimethylethyl 2,3-dihydro-7-[[[2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]amino]carbonyl]-1H-indole-1-carboxylate

To a stirring solution of 1,1-dimethylethyl 2,3-dihydro-1H-indole-1-carboxylate (Aldrich, 1.0 g, 4.5 mmol), N,N,N'N'-tetramethylethylenediamine (0.90 mL, 690 mg, 6.0 mmol), and anhydrous Et2O (20 mL) at -78 °C, was added sec-butyllithium (4.2 mL, 5.4 mmol, 1.3 M in cyclohexane) dropwise over a 10 min period. The resulting solution was stirred at -78 °C for 1 hour followed by the dropwise addition of 2-methyl-4-heptafluoroisopropylphenyl isocyanate (1.4 g, 4.5 mmol) over a 4 min period. The solution was allowed to warm to room temperature over 1 hour followed by the addition of saturated aqueous NH4Cl (4 mL). The mixture was partitioned between Et2O and H2O. The combined organic extract was dried (MgSO4) and concentrated in vacuo. The residue was subjected to chromatography on silica gel with 30% EtOAc/hexanes as eluent to give the title compound of Step A (1.6 g, 3.1 mmol, 69% yield) as a white solid:

1H NMR (CDCl3) δ 1.29 (s, 9H), 2.32 (s, 3H), 3.12 (t, 2H), 4.18 (t, 2H), 7.16 (t, 1H), 7.31-7.39 (m, 2H), 7.43 (d, 1H), 7.61 (d, 1H), 7.81 (bs, 1H), 8.59 (d, 1H).

Step B: Preparation of 2,3-dihydro-N-[2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-1H-indole-7-carboxamide

A solution of 1,1-dimethylethyl 2,3-dihydro-7-[[[2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]amino]carbonyl]-1H-indole-1-carboxylate (i.e. the product from Step A) (1.1 g, 2.1 mmol), trifluoroacetic acid (15 mL), and CH2Cl2 (50 ml) was stirred at room temperature for 2 hours. The solution was carefully poured into a saturated aqueous solution of NaHCO3 (500 mL). The mixture was partitioned between CH2Cl2 and H2O. The combined organic extract was dried (MgSO4) and concentrated in vacuo. The residue was subjected to chromatography on silica gel with 30% EtOAc/hexanes as eluent to give the title compound (800 mg, 1.9 mmol, 90% yield) as a white solid

1H NMR (CDCl3) δ 2.40 (s, 3H), 3.08 (t, 2H), 3.73 (t, 2H), 6.37 (bs, 1H), 6.63(t, 1H), 7.18-7.28 (m, 3H), 7.47 (d, 1H), 7.80 (s, 1H), 8.22(d, 1H).

Step C: Preparation of 2,3-dihydro-N1-(1-methylethyl)-N7-[2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-1H-indole-1,7-dicarboxamide

A solution of the product of Step B (200 mg, 0.48 mmol), isopropyl isocyanate (0.10 mL, 87 mg, 1.00 mmol), and CH2Cl2 (10 ml) was stirred at room temperature for 17 hours. The mixture was filtered and the residue was washed with a 1/1 solution of Et2O/CH2Cl2 (3 mL) to give the title compound (1.6 g, 3.1 mmol, 69% yield), a compound of this invention, as a white solid.

1H NMR (DMSO-d6) δ 0.98 (d, 6H), 2.37 (s, 3H), 3.21 (t, 2H), 3.62-3.71 (m, 1H), 4.01 (t, 1H), 6.73 (d, 1H), 7.00 (t, 1H), 7.32(d, 2H), 7.41-7.45 (m, 2H), 8.14 (d, 1H), 9.24 (s, 1H).

By the procedures described herein together with methods known in the art, the following compounds of Tables 1 to 14 can be prepared. The following abbreviations are used in the Tables: t is tertiary, s is secondary, n is normal, i is iso, c is cyclo, Me is methyl, Et is ethyl, Pr is propyl, i-Pr is isopropyl, t-Bu is tert butyl, Ph is phenyl, OMe is methoxy, OEt is ethoxy, SMe is methylthio, SEt is ethylthio, CN is cyano, NO2 is nitro, TMS is trimethylsilyl, S(O)Me is methylsulfinyl, and S(O)2Me is methylsulfonyl.

Formulation/Utility

Compounds of this invention will generally be used as a formulation or composition with an agriculturally suitable carrier comprising at least one of a liquid diluent, a solid diluent or a surfactant. 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 liquids such as solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and/or suspoemulsions) and the like which optionally can be thickened into gels. Useful formulations further include solids such as dusts, powders, granules, pellets, tablets, films, and the like which can be water-dispersible ("wettable") or water-soluble. 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. Sprayable formulations can be extended in suitable media and used at spray volumes from about one to several hundred liters per hectare. High-strength compositions are primarily used as intermediates for further formulation.

The formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges that add up to 100 percent by weight. Weight Percent Active Ingredient Diluent Surfactant Water-Dispersible and Water-soluble Granules, Tablets and Powders. 5-90 0-94 1-15 Suspensions, Emulsions, Solutions (including Emulsifiable Concentrates) 5-50 40-95 0-15 Dusts 1-25 70-99 0-5 Granules and Pellets

High Strength Compositions
0.01-99

90-99
5-99.99

0-10
0-15

0-2

Typical solid diluents are described in Watkins, et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950.McCutcheon's Detergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, New Jersey, as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth and the like, or thickeners to increase viscosity.

Surfactants include, for example, polyethoxylated alcohols, polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acid esters, dialkyl sulfosuccinates, alkyl sulfates, alkylbenzene sulfonates, organosilicones, N,N-dialkyltaurates, lignin sulfonates, naphthalene sulfonate formaldehyde condensates, polycarboxylates, and polyoxyethylene/polyoxypropylene block copolymers. Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, starch, sugar, silica, talc, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate. Liquid diluents include, for example, water, N,N-dimethylformamide, dimethyl sulfoxide, N-alkylpyrrolidone, ethylene glycol, polypropylene glycol, paraffins, alkylbenzenes, alkylnaphthalenes, oils of olive, castor, linseed, tung, sesame, com, peanut, cotton-seed, soybean, rape-seed and coconut, fatty acid esters, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, and alcohols such as methanol, cyclohexanol, decanol and tetrahydrofurfuryl alcohol.

Solutions, including emulsifiable concentrates, can be prepared by simply mixing the ingredients. Dusts and powders can be prepared by blending and, usually, grinding as in a hammer mill or fluid-energy mill. Suspensions are usually prepared by wet-milling; see, for example, U.S. 3,060,084. 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 PCT Publication 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 Modem 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; and Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989.

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. Example A 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 B Granule Compound 1 10.0% attapulgite granules (low volatile matter, 0.71/0.30 mm; U.S.S. No. 25-50 sieves) 90.0%.
Example C Ewxtruded 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 D Emulsifiable Concentrate Compound 1 20.0% blend of oil soluble sulfonates and polyoxyethylene ethers 10.0% isophorone 70.0%.
Example E Granule Compound 1 0.5% cellulose 2.5% lactose 4.0% cornmeal 93.0%.

Compounds of this invention are characterized by favorable metabolic and/or soil residual patterns and exhibit activity controlling a spectrum of agronomic and nonagronomic invertebrate pests. (In the context of this disclosure "invertebrate pest control" means inhibition of invertebrate pest development (including mortality) that causes significant reduction in feeding or other injury or damage caused by the pest; related expressions are defined analogously.) As referred to in this disclosure, the term "invertebrate pest" includes arthropods, gastropods and nematodes of economic importance as pests. The term "arthropod" includes insects, mites, spiders, scorpions, centipedes, millipedes, pill bugs and symphylans. The term "gastropod" includes snails, slugs and other Stylommatophora. The term "nematode" includes all of the helminths, such as: roundworms, heartworms, and phytophagous nematodes (Nematoda), flukes (Tematoda), Acanthocephala, and tapeworms (Cestoda). Those skilled in the art will recognize that not all compounds are equally effective against all pests. Compounds of this invention display activity against economically important agronomic, forest, greenhouse, nursery, ornamentals, food and fiber, public and animal health, domestic and commercial structure, household, and stored product pests. These include larvae of the order Lepidoptera, such as armyworms, cutworms, loopers, and heliothines in the family Noctuidae (e.g., fall armyworm (Spodoptera fugiperda J. E. Smith), beet armyworm (Spodoptera exigua Hübner), black cutworm (Agrotis ipsilon Hufnagel), cabbage looper (Trichoplusia ni Hübner), tobacco budworm (Heliothis virescens Fabricius)); borers, casebearers, webworms, coneworms, cabbageworms and skeletonizers from the family Pyralidae (e.g., European corn borer (Ostrinia nubilalis Hübner), navel orangeworm (Amyelois transitella Walker), corn root webworm (Crambus caliginosellus Clemens), sod webworm (Herpetogramma licarsisalis Walker)); leafrollers, budworms, seed worms, and fruit worms in the family Tortricidae (e.g., codling moth (Cydia pomonella Linnaeus), grape berry moth (Endopiza viteana Clemens), oriental fruit moth (Grapholita molesta Busck)); and many other economically important lepidoptera (e.g., diamondback moth (Plutella xylostella Linnaeus), pink bollworm (Pectinophora gossypiella Saunders), gypsy moth (Lymantria dispar Linnaeus)); nymphs and adults of the order Blattodea including cockroaches from the families Blattellidae and Blattidae (e.g., oriental cockroach (Blatta orientalis Linnaeus), Asian cockroach (Blatella asahinai Mizukubo), German cockroach (Blattella germanica Linnaeus), brownbanded cockroach (Supella longipalpa Fabricius), American cockroach(Periplaneta americana Linnaeus), brown cockroach (Periplaneta brunnea Burmeister), Madeira cockroach (Leucophaea maderae Fabricius)); foliar feeding larvae and adults of the order Coleoptera including weevils from the families Anthribidae, Bruchidae, and Curculionidae (e.g., boll weevil (Anthonomus grandis Boheman), rice water weevil(Lissorhoptrus oryzophilus Kuschel), granary weevil (Sitophilus granarius Linnaeus), rice weevil (Sitophilus oryzae Linnaeus)); flea beetles, cucumber beetles, rootworms, leaf beetles, potato beetles, and leafminers in the family Chrysomelidae (e.g., Colorado potato beetle (Leptinotarsa decemlineata Say), western corn rootworm (Diabrotica virgifera virgifera LeConte)); chafers and other beetles from the family Scaribaeidae (e.g., Japanese beetle (Popillia japonica Newman) and European chafer (Rhizotrogus majalis Razoumowsky)); carpet beetles from the family Dermestidae; wireworms from the family Elateridae; bark beetles from the family Scolytidae and flour beetles from the family Tenebrionidae. In addition it includes: adults and larvae of the order Dermaptera including earwigs from the family Forficulidae (e.g., European earwig (Forficula auricularia Linnaeus), black earwig (Chelisoches morio Fabricius)); adults and nymphs of the orders Hemiptera and Homoptera such as, plant bugs from the family Miridae, cicadas from the family Cicadidae, leafhoppers (e.g. Empoasca spp.) from the family Cicadellidae, planthoppers from the families Fulgoroidae and Delphacidae, treehoppers from the family Membracidae, psyllids from the family Psyllidae, whiteflies from the family Aleyrodidae, aphids from the family Aphididae, phylloxera from the family Phylloxeridae, mealybugs from the family Pseudococcidae, scales from the families Coccidae, Diaspididae and Margarodidae, lace bugs from the family Tingidae, stink bugs from the family Pentatomidae, cinch bugs (e.g., Blissus spp.) and other seed bugs from the family Lygaeidae, spittlebugs from the family Cercopidae squash bugs from the family Coreidae, and red bugs and cotton stainers from the family Pyrrhocoridae. Also included are adults and larvae of the order Acari (mites) such as spider mites and red mites in the family Tetranychidae (e.g., European red mite (Panonychus ulmi Koch), two spotted spider mite (Tetranychus urticae Koch), McDaniel mite (Tetranychus mcdanieli McGregor)), flat mites in the family Tenuipalpidae (e.g., citrus flat mite (Brevipalpus lewisi McGregor)), rust and bud mites in the family Eriophyidae and other foliar feeding mites and mites important in human and animal health, i.e. dust mites in the family Epidermoptidae, follicle mites in the family Demodicidae, grain mites in the family Glycyphagidae, ticks in the order Ixodidae (e.g., deer tick (Ixodes scapularis Say), Australian paralysis tick (Ixodes holocyclus Neumann), American dog tick(Dermacentor variabilis Say), lone star tick (Amblyomma americanum Linnaeus) and scab and itch mites in the families Psoroptidae, Pyemotidae, and Sarcoptidae; adults and immatures of the order Orthoptera including grasshoppers, locusts and crickets (e.g., migratory grasshoppers (e.g., Melanoplus sanguinipes Fabricius, M differentialis Thomas), American grasshoppers (e.g., Schistocerca americana Drury), desert locust (Schistocerca gregaria Forskal), migratory locust (Locusta migratoria Linnaeus), house cricket (Acheta domesticus Linnaeus), mole crickets (Gryllotalpa spp.)); adults and immatures of the order Diptera including leafminers, midges, fruit flies (Tephritidae), frit flies (e.g., Oscinella frit Linnaeus), soil maggots, house flies (e.g., Musca domestica Linnaeus), lesser house flies (e.g., Fannia canicularis Linnaeus, F. femoralis Stein), stable flies (e.g., Stomoxys calcitrans Linnaeus), face flies, horn flies, blow flies (e.g., Chrysomya spp., Phormia spp.), and other muscoid fly pests, horse flies (e.g., Tabanus spp.), bot flies (e.g., Gastrophilus spp., Oestrus spp.), cattle grubs (e.g., Hypoderma spp.), deer flies (e.g., Chrysops spp.), keds (e.g.,Melophagus ovinus Linnaeus) and other Brachycera, mosquitoes (e.g., Aedes spp.,Anopheles spp., Culex spp.), black flies (e.g., Prosimulium spp., Simulium spp.), biting midges, sand flies, sciarids, and other Nematocera; adults and immatures of the order Thysanoptera including onion thrips (Thrips tabaci Lindeman) and other foliar feeding thrips; insect pests of the order Hymenoptera including ants (e.g., red carpenter ant(Camponotus ferrugineus Fabricius), black carpenter ant (Camponotus pennsylvanicus De Geer), Pharaoh ant (Monomorium pharaonis Linnaeus), little fire ant (Wasmannia auropunctata Roger), fire ant (Solenopsis geminata Fabricius), red imported fire ant(Solenopsis invicta Buren), Argentine ant (Iridomyrmex humilis Mayr), crazy ant(Paratrechina longicornis Latreille), pavement ant (Tetramorium caespitum Linnaeus), cornfield ant (Lasius alienus Förster), odorous house ant (Tapinoma sessile Say)), bees (including carpenter bees), hornets, yellow jackets and wasps; insect pests of the order Isoptera including the eastern subterranean termite (Reticulitermes flavipes Kollar), western subterranean termite (Reticulitermes hesperus Banks), Formosan subterranean termite (Coptotermes formosanus Shiraki), West Indian drywood termite (Incisitermes immigrans Snyder) and other termites of economic importance; insect pests of the order Thysanura such as silverfish (Lepisma saccharina Linnaeus) and firebrat (Thermobia domestica Packard); insect pests of the order Mallophaga and including the head louse (Pediculus humanus capitis De Geer), body louse (Pediculus humanus humanus Linnaeus), chicken body louse(Menacanthus stramineus Nitszch), dog biting louse (Trichodectes canis De Geer), fluff louse (Goniocotes gallinae De Geer), sheep body louse (Bovicola ovis Schrank), short-nosed cattle louse (Haematopinus eurysternus Nitzsch), long-nosed cattle louse (Linognathus vituli Linnaeus) and other sucking and chewing parasitic lice that attack man and animals; insect pests of the order Siphonoptera including the oriental rat flea (Xenopsylla cheopis Rothschild), cat flea (Ctenocephalides felis Bouche), dog flea (Ctenocephalides canis Curtis), hen flea (Ceratophyllus gallinae Schrank), sticktight flea (Echidnophaga gallinacea Westwood), human flea (Pulex irritans Linnaeus) and other fleas afflicting mammals and birds. Additional arthropod pests covered include: spiders in the order Araneae such as the brown recluse spider (Loxosceles reclusa Gertsch & Mulaik) and the black widow spider(Latrodectus mactans Fabricius), and centipedes in the order Scutigeromorpha such as the house centipede (Scutigera coleoptrata Linnaeus). Activity also includes members of the Classes Nematoda, Cestoda, Trematoda, and Acanthocephala including economically important members of the orders Strongylida, Ascaridida, Oxyurida, Rhabditida, Spirurida, and Enoplida such as but not limited to economically important agricultural pests (i.e. root knot nematodes in the genus Meloidogyne, lesion nematodes in the genus Pratylenchus, stubby root nematodes in the genus Trichodorus, etc.) and animal and human health pests (i.e. all economically important flukes, tapeworms, and roundworms, such as Strongylus vulgaris in horses, Toxocara canis in dogs, Haemonchus contortus in sheep, Dirofilaria immitis Leidy in dogs, Anoplocephala perfoliata in horses, Fasciola hepatica Linnaeus in ruminants, etc.).

Compounds of the invention show particularly high activity against pests in the order Lepidoptera (e.g., Alabama argillacea Hübner (cotton leaf worm), Archips argyrospila Walker (fruit tree leaf roller), A. rosana Linnaeus (European leaf roller) and other Archips species, Chilo suppressalis Walker (rice stem borer), Cnaphalocrosis medinalis Guenee (rice leaf roller), Crambus caliginosellus Clemens (corn root webworm), Crambus teterrellus Zincken (bluegrass webworm), Cydia pomonella Linnaeus (codling moth), Earias insulana Boisduval (spiny bollworm), Earias vittella Fabricius (spotted bollworm), Helicoverpa armigera Hübner (American bollworm), Helicoverpa zea Boddie (com earworm), Heliothis virescens Fabricius (tobacco budworm), Herpetogramma licarsisalis Walker (sod webworm), Lobesia botrana Denis & Schiffermüller (grape berry moth), Pectinophora gossypiella Saunders (pink bollworm), Phyllocnistis citrella Stainton (citrus leafminer),Pieris brassicae Linnaeus (large white butterfly), Pieris rapae Linnaeus (small white butterfly), Plutella xylostella Linnaeus (diamondback moth), Spodoptera exigua Hübner (beet armyworm), Spodoptera litura Fabricius (tobacco cutworm, cluster caterpillar),Spodoptera frugiperda J. E. Smith (fall armyworm), Trichoplusia ni Hübner (cabbage looper) and Tuta absoluta Meyrick (tomato leafminer)). Compounds of the invention also have commercially significant activity on members from the order Homoptera including:Acyrthisiphon pisum Harris (pea aphid), Aphis craccivora Koch (cowpea aphid), Aphis fabae Scopoli (black bean aphid), Aphis gossypii Glover (cotton aphid, melon aphid), Aphis pomi De Geer (apple aphid), Aphis spiraecola Patch (spirea aphid), Aulacorthum solani Kaltenbach (foxglove aphid), Chaetosiphon fragaefolii Cockerell (strawberry aphid),Diuraphis noxia Kurdjumov/Mordvilko (Russian wheat aphid), Dysaphis plantaginea Paaserini (rosy apple aphid), Eriosoma lanigerum Hausmann (woolly apple aphid),Hyalopterus pruni Geoffroy (mealy plum aphid), Lipaphis erysimi Kaltenbach (turnip aphid), Metopolophium dirrhodum Walker (cereal aphid), Macrosipum euphorbiae Thomas (potato aphid), Myzus persicae Sulzer (peach-potato aphid, green peach aphid), Nasonovia ribisnigri Mosley (lettuce aphid), Pemphigus spp. (root aphids and gall aphids),Rhopalosiphum maidis Fitch (com leaf aphid), Rhopalosiphum padi Linnaeus (bird cherryoat aphid), Schizaphis graminum Rondani (greenbug), Sitobion avenae Fabricius (English grain aphid), Therioaphis maculata Buckton (spotted alfalfa aphid), Toxoptera aurantii Boyer de Fonscolombe (black citrus aphid), and Toxoptera citricida Kirkaldy (brown citrus aphid); Adelges spp. (adelgids); Phylloxera devastatrix Pergande (pecan phylloxera);Bemisia tabaci Gennadius (tobacco whitefly, sweetpotato whitefly), Bemisia argentifolii Bellows & Perring (silverleaf whitefly), Dialeurodes citri Ashmead (citrus whitefly) andTrialeurodes vaporariorum Westwood (greenhouse whitefly); Empoasca fabae Harris (potato leafhopper), Laodelphax striatellus Fallen (smaller brown planthopper), Macrolestes quadrilineatus Forbes (aster leafhopper), Nephotettix cinticeps Uhler (green leafhopper),Nephotettix nigropictus Stål (rice leafhopper), Nilaparvata lugens Stål (brown planthopper),Peregrinus maidis Ashmead (com planthopper), Sogatella furcifera Horvath (white-backed planthopper), Sogatodes orizicola Muir (rice delphacid), Typhlocyba pomaria McAtee white apple leafhopper, Erythroneoura spp. (grape leafhoppers); Magicidada septendecim Linnaeus (periodical cicada); Icerya purchasi Maskell (cottony cushion scale),Quadraspidiotus perniciosus Comstock (San Jose scale); Planococcus citri Risso (citrus mealybug); Pseudococcus spp. (other mealybug complex); Cacopsylla pyricola Foerster (pear psylla), Trioza diospyri Ashmead (persimmon psylla). These compounds also have activity on members from the order Hemiptera including: Acrosternum hilare Say (green stink bug), Anasa tristis De Geer (squash bug), Blissus leucopterus leucopterus Say (chinch bug), Corythuca gossypii Fabricius (cotton lace bug), Cyrtopeltis modesta Distant (tomato bug), Dysdercus suturellus Herrich-Schäffer (cotton stainer), Euchistus servus Say (brown stink bug), Euchistus variolarius Palisot de Beauvois (one-spotted stink bug), Graptosthetus spp. (complex of seed bugs), Leptoglossus corculus Say (leaf-footed pine seed bug), Lygus lineolaris Palisot de Beauvois (tarnished plant bug), Nezara viridula Linnaeus (southern green stink bug), Oebalus pugnax Fabricius (rice stink bug), Oncopeltus fasciatus Dallas (large milkweed bug), Pseudatomoscelis seriatus Reuter (cotton fleahopper). Other insect orders controlled by compounds of the invention include Thysanoptera (e.g., Frankliniella occidentalis Pergande (western flower thrip), Scirthothrips citri Moulton (citrus thrip),Sericothrips variabilis Beach (soybean thrip), and Thrips tabaci Lindeman (onion thrip); and the order Coleoptera (e.g., Leptinotarsa decemlineata Say (Colorado potato beetle),Epilachna varivestis Mulsant (Mexican bean beetle) and wireworms of the genera Agriotes, Athous or Limonius).

In accordance with this invention, compounds of Formula I, their N-oxides or salts thereof, and/or compounds of Formula II, their N-oxides or salts thereof, can be mixed with one or more other biologically active compounds or agents, e.g. a compound different from a compound of Formula I and/or Formula II and their N-oxides and salts, as the case may be, including insecticides, fungicides, nematocides, bactericides, acaricides, growth regulators such as rooting stimulants, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants, other biologically active compounds or entomopathogenic bacteria, virus or fungi to form a multi-component pesticide giving an even broader spectrum of agricultural utility. Thus, compositions of the present invention comprising at least one Formula I compound and/or Formula II compound can also comprise at least one other biologically active compound or agent selected from the group consisting of an other insecticide, a fungicide, a nematocide, a bactericide, an acaricide, a growth regulator, a rooting stimulant, a chemosteilant, a semiochemical, a repellent, an attractant, a pheromone, a feeding stimulant, and an entomopathogenic bacterium, virus or fungus. Such compositions can further comprise at least one additional component selected from the group consisting of a surfactant, a solid diluent, and a liquid diluent.

Examples of other biologically active compounds or agents useful in this invention include: insecticides such as abamectin, acephate, acetamiprid, avermectin, azadirachtin, azinphos-methyl, bifenthrin, binfenazate, buprofezin, carbofuran, chlorfenapyr, chlorfluazuron, chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clothianidin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, cypermethrin, cyromazine, deltamethrin, diafenthiuron, diazinon, diflubenzuron, dimethoate, diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, fenothicarb, fenoxycarb, fenpropathrin, fenproximate, fenvalerate, fipronil, flonicamid, flucythrinate, tau-fluvalinate, flufenoxuron, fonophos, halofenozide, hexaflumuron, imidacloprid, indoxacarb, isofenphos, lufenuron, malathion, metaldehyde, methamidophos, methidathion, methomyl, methoprene, methoxychlor, monocrotophos, methoxyfenozide, nithiazin, novaluron, oxamyl, parathion, parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, pymetrozine, pyridalyl, pyriproxyfen, rotenone, spinosad, sulprofos, tebufenozide, teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tralomethrin, trichlorfon and triflumuron; fungicides such as acibenzolar, azoxystrobin, benomyl, blasticidin-S, Bordeaux mixture (tribasic copper sulfate), bromuconazole, carpropamid, captafol, captan, carbendazim, chloroneb, chlorothalonil, copper oxychloride, copper salts, cyflufenamid, cymoxanil, cyproconazole, cyprodinil, (S)-3,5-dichloro-N-(3-chloro-1-ethyl-1-methyl-2-oxopropyl)-4-methylbenzamide (RH 7281), diclocymet (S-2900), diclomezine, dicloran, difenoconazole, (S)-3,5-dihydro-5-methyl-2-(methylthio)-5-phenyl-3-(phenylamino)-4H-imidazol-4-one (RP 407213), dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dodine, edifenphos, epoxiconazole, famoxadone, fenamidone, fenarimol, fenbuconazole, fencaramid (SZX0722), fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, fluazinam, fludioxonil, flumetover (RPA 403397), fluquinconazole, flusilazole, flutolanil, flutriafol, folpet, fosetyl-aluminum, furalaxyl, furametapyr (S-82658), hexaconazole, ipconazole, iprobenfos, iprodione, isoprothiolane, kasugamycin, kresoxim-methyl, mancozeb, maneb, mefenoxam, mepronil, metalaxyl, metconazole, metominostrobin/fenominostrobin (SSF-126), myclobutanil, neo-asozin (ferric methanearsonate), oxadixyl, penconazole, pencycuron, probenazole, prochloraz, propamocarb, propiconazole, pyrifenox, pyraclostrobin, pyrimethanil, pyroquilon, quinoxyfen, spiroxamine, sulfur, tebuconazole, tetraconazole, thiabendazole, thifluzamide, thiophanate-methyl, thiram, tiadinil, triadimefon, triadimenol, tricyclazole, trifloxystrobin, triticonazole, validamycin and vinclozolin; nematocides such as aldicarb, oxamyl and fenamiphos; bactericides such as streptomycin; acaricides such as amitraz, chinomethionat, chlorobenzilate, cyhexatin, dicofol, dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpropathrin, fenpyroximate, hexythiazox, propargite, pyridaben and tebufenpyrad; and biological agents such as Bacillus thuringiensis including ssp. aizawai and kurstaki, Bacillus thuringiensis delta endotoxin, baculovirus, and entomopathogenic bacteria, virus and fungi.

A general reference for these agricultural protectants is The Pesticide Manual, 12th Edition, C. D. S. Tomlin, Ed., British Crop Protection Council, Farnham, Surrey, U.K., 2000.

Of note are compositions which comprise at least one compound selected from the group consisting of a compound of Formula I, an N-oxide or a salt thereof, and a compound of Formula II, an N-oxide or a salt thereof; and at least one other biologically active compound or agent selected from the group consisting of abamectin, acephate, acetamiprid, avermectin, azadirachtin, azinphos-methyl, bifenthrin, binfenazate, buprofezin, carbofuran, chlorfenapyr, chlorfluazuron, chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clothianidin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, cypermethrin, cyromazine, deltamethrin, diafenthiuron, diazinon, diflubenzuron, dimethoate, diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, fenothicarb, fenoxycarb, fenpropathrin, fenproximate, fenvalerate, fipronil, flonicamid, flucythrinate, tau-fluvalinate, flufenoxuron, fonophos, halofenozide, hexaflumuron, imidacloprid, indoxacarb, isofenphos, lufenuron, malathion, metaldehyde, methamidophos, methidathion, methomyl, methoprene, methoxychlor, monocrotophos, methoxyfenozide, nithiazin, novaluron, oxamyl, parathion, parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, pymetrozine, pyridalyl, pyriproxyfen, rotenone, spinosad, sulprofos, tebufenozide, teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tralomethrin, trichlorfon and triflumuron, aldicarb, oxamyl, fenamiphos, amitraz, chinomethionat, chlorobenzilate, cyhexatin, dicofol, dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpropathrin, fenpyroximate, hexythiazox, propargite, pyridaben, tebufenpyrad, Bacillus thuringiensis, Bacillus thuringiensis delta endotoxin, baculovirus, and entomopathogenic bacteria, virus and fungi.

Preferred compositions include compositions which comprise at least one compound selected from the group consisting of a compound of Formula I, an N-oxide or a salt thereof and a compound of Formula II, an N-oxide or a salt thereof; and at least one other biologically active compound or agent selected from the group consisting of a pyrethroid (e.g. cypermethrin, cyhalothrin, cyfluthrin, beta-cyfluthrin, esfenvalerate, fenvalerate and tralomethrin); a carbamate (e.g. fenothicarb, methomyl, oxamyl and thiodicarb); a neonicotinoid (e.g. clothianidin, imidacloprid and thiacloprid); a neuronal sodium channel blocker (e.g. indoxacarb); an insecticidal macrocyclic lactone (e.g. spinosad, abamectin, avermectin and emamectin); a γ-aminobutyric acid (GABA) antagonist (e.g. endosulfan, ethiprole and fipronil); an insecticidal urea (e.g. flufenoxuron and triflumuron); a juvenile hormone mimic (e.g. diofenolan and pyriproxyfen); pymetrozine; and amitraz. Preferred other biologically active agents useful in compositions of this invention include Bacillus thuringiensis and Bacillus thuringiensis delta endotoxin as well as naturally occurring and genetically modified viral insecticides including members of the family Baculoviridae as well as entomophagous fungi.

Of note are preferred compositions which comprise at least one compound selected from the group consisting of a compound of Formula I, an N-oxide or a salt thereof, and a compound of Formula II, an N-oxide or a salt thereof; and at least one biologically active compound or agent selected from the group consisting of cypermethrin, cyhalothrin, cyfluthrin, beta-cyfluthrin, esfenvalerate, fenvalerate, tralomethrin, fenothicarb, methomyl, oxamyl, thiodicarb, clothianidin, imidacloprid, thiacloprid, indoxacarb, spinosad, abamectin, avermectin, emamectin, endosulfan, ethiprole, fipronil, flufenoxuron, triflumuron, diofenolan, pyriproxyfen, pymetrozine, amitraz, Bacillus thuringiensis, Bacillus thuringiensis delta endotoxin and entomophagous fungi.

Most preferred mixtures useful in the compositions and methods of this invention include a mixture of a compound of this invention with cyhalothrin; a mixture of a compound of this invention with cyfluthrin; a mixture of a compound of this invention with beta-cyfluthrin; a mixture of a compound of this invention with esfenvalerate; a mixture of a compound of this invention with methomyl; a mixture of a compound of this invention with imidacloprid; a mixture of a compound of this invention with thiacloprid; a mixture of a compound of this invention with indoxacarb; a mixture of a compound of this invention with abamectin; a mixture of a compound of this invention with endosulfan; a mixture of a compound of this invention with ethiprole; a mixture of a compound of this invention with fipronil; a mixture of a compound of this invention with flufenoxuron; a mixture of a compound of this invention with pyriproxyfen; a mixture of a compound of this invention with pymetrozine; a mixture of a compound of this invention with amitraz; a mixture of a compound of this invention with Bacillus thuringiensis and a mixture of a compound of this invention with Bacillus thuringiensis delta endotoxin.

In certain instances, combinations with other invertebrate pest control compounds or agents having a similar spectrum of control but a different mode of action will be particularly advantageous for resistance management. Thus, compositions and methods of the present invention can further comprise or utilize a biologically effective amount of at least one other invertebrate pest control compound or agent having a similar spectrum of control but a different mode of action from the compound of the invention. Contacting a plant genetically modified to express a plant protection compound (e.g., protein) or the locus of the plant with a biologically effective amount of a compound of this invention can also provide a broader spectrum of plant protection and be advantageous for resistance management.

At least one invertebrate pest is controlled and protection of agronomic, horticultural and specialty crops, animal and human health is achieved by applying, one or more of the compounds or compositions of this invention, in a biologically effective amount, to the environment of the pest including the agronomic and/or nonagronomic locus of infestation, to the area to be protected, or directly on the pest to be controlled. Thus, the present invention further comprises a method for the control of at least one foliar- or soil-inhabiting invertebrate and/or protection of agronomic and/or nonagronomic environments, comprising contacting the invertebrate pest or its environment with a biologically effective amount of one or more of the compounds of the invention, or with a biologically effective amount of a composition comprising at least one such compound, or with a composition comprising at least one such compound and a biologically effective amount of at least biologically effective amount of a one other biologically active compound or agent. Examples of suitable compositions comprising at least one compound of the invention and at least one other biologically active compound or agent include granular compositions wherein the other biologically active compound is present on the same granule as the compound of the invention or on a granule that is separate from the granule where the compound of this invention is present.

A preferred method of contact is by spraying. Alternatively, a granular composition comprising a compound of the invention can be applied to the plant foliage or the soil. Compounds of this invention are effective in delivery through plant uptake by contacting the plant with a composition comprising a compound of this invention applied as a soil drench of a liquid formulation, a granular formulation to the soil, a nursery box treatment or a dip of transplants. Other methods of contact include application of a compound or a composition of the invention by direct and residual sprays, aerial sprays, seed coats, microencapsulations, systemic uptake, baits, eartags, boluses, foggers, fumigants, aerosols, dusts and many others.

The compounds of this invention can be incorporated into baits that are consumed by the invertebrates or within devices such as traps and the like. Granules or baits comprising between 0.01-5% active ingredient, 0.05-10% moisture retaining agent(s) and 40-99% vegetable flour are effective in controlling soil insects at very low application rates, particularly at doses of active ingredient that are lethal by ingestion rather than by direct contact.

The compounds of this invention can be applied in their pure state, but most often application will be of a formulation comprising one or more compounds with suitable carriers, diluents, and surfactants and possibly in combination with a food depending on the contemplated end use. A preferred method of application involves spraying a water dispersion or refined oil solution of the compounds. Combinations with spray oils, spray oil concentrations, spreader stickers, adjuvants, other solvents, and synergists such as piperonyl butoxide often enhance compound efficacy.

The rate of application required for effective control (i.e. "biologically effective amount") will depend on such factors as the species of invertebrate to be controlled, the pest's life cycle, life stage, its size, location, time of year, host crop or animal, feeding behavior, mating behavior, ambient moisture, temperature, and the like. Under normal circumstances, application rates of about 0.01 to 2 kg of active ingredient per hectare are sufficient to control pests in agronomic ecosystems, but as little as 0.0001 kg/hectare may be sufficient or as much as 8 kg/hectare may be required. For nonagronomic applications, effective use rates will range from about 1.0 to 50 mg/square meter but as little as 0.1 mg/square meter may be sufficient or as much as 150 mg/square meter may be required. One skilled in the art can easily determine the biologically effective amount necessary for the desired level of invertebrate pest control.

The following Tests in the Biological Examples of the Invention demonstrate the control efficacy of compounds of this invention on specific pests. "Control efficacy" represents inhibition of arthropod development (including mortality) that causes significantly reduced feeding. The pest control protection afforded by the compounds is not limited, however, to these species. See Index Tables A-E for compound descriptions. The following abbreviations are used in the Index Tables that follow: t is tertiary, n is normal, i is iso, s is secondary, Me is methyl, Et is ethyl, Pr is propyl and Bu is butyl; accordinglyi-Pr is isopropyl, s-Bu is secondary butyl, etc. Ac is COCH3. The abbreviation "Ex." stands for "Example" and is followed by a number indicating in which example the compound is prepared.

BIOLOGICAL EXAMPLES OF THE INVENTION TEST A

For evaluating control of fall armyworm (Spodoptera frugiperda) the test unit consisted of a small open container with a 4-5-day-old corn (maize) plant inside. This was pre-infested with 10-15 1-day-old larvae on a piece of insect diet by use of a core sampler to remove a plug from a sheet of hardened insect diet having many larvae growing on it and transfer the plug containing larvae and diet to the test unit. The larvae moved onto the test plant as the diet plug dried out.

Test compounds were formulated using a solution containing 10% acetone, 90% water and 300 ppm X-77® Spreader Lo-Foam Formula non-ionic surfactant containing alkylarylpolyoxyethylene, free fatty acids, glycols and isopropanol (Loveland Industries, Inc. Greeley, Colorado, USA), unless otherwise indicated. The formulated compounds were applied in 1 mL of liquid through a SUJ2 atomizer nozzle with 1/8 JJ custom body (Spraying Systems Co. Wheaton, Illinois, USA) positioned 1.27 cm (0.5 inches) above the top of each test unit. All experimental compounds in this screen were sprayed at 50 ppm and replicated three times. After spraying of the formulated test compound, each test unit was allowed to dry for 1 hour and then a black, screened cap was placed on top. The test units were held for 6 days in a growth chamber at 25 °C and 70% relative humidity. Plant feeding damage was then visually assessed.

Of the compounds tested, the following provided excellent levels of plant protection (10% or less feeding damage): 1, 2, 4, 5, 21 and 33.

TEST B

For evaluating control of tobacco budworm (Heliothis virescens) the test unit consisted of a small open container with a 6-7 day old cotton plant inside. This was pre-infested with 8 2-day-old larvae on a piece of insect diet by use of a core sampler as described for Test A.

Test compounds were formulated and sprayed at 50 ppm as described for Test A. The applications were replicated three times. After spraying, the test units were maintained in a growth chamber and then visually rated as described for Test A.

Of the compounds tested, the following provided excellent levels of plant protection (10% or less feeding damage): 1 and 2.

TEST C

For evaluating control of diamondback moth (Plutella xylostella) the test unit consisted of a small open container with a 12-14-day-old radish plant inside. This was pre-infested with 10-15 neonate larvae on a piece of insect diet by use of a core sampler as described for Test A.

Test compounds were formulated and sprayed at 50 ppm as described for Test A. The applications were replicated three times. After spraying, the test units were maintained in a growth chamber and then visually rated as described for Test A.

Of the compounds tested, the following provided excellent levels of plant protection (10% or less feeding damage): 1, 2, 4, 5, 21, 25 and 33.

TEST D

For evaluating control of beet armyworm (Spodoptera exigua) the test unit consisted of a small open container with a 4-5-day-old corn plant inside. This was pre-infested with 10-15 1-day-old larvae on a piece of insect diet by use of a core sampler as described for Test A.

Test compounds were formulated and sprayed at 50 ppm as described for Test A. The applications were replicated three times. After spraying, the test units were maintained in a growth chamber and then visually rated as described for Test A.

Of the compounds tested, the following provided excellent levels of plant protection (10% or less feeding damage): 4.


Anspruch[de]
  1. Verfahren zur Kontrolle von mindestens einem wirbellosen Schädling, umfassend: Kontaktieren des wirbellosen Schädlings oder seiner Umgebung mit einer biologisch wirksamen Menge von mindestens einer Verbindung, die aus der Gruppe ausgewählt ist, bestehend aus einer Verbindung der Formel I, einem N-Oxid oder einem Salz davon und einer Verbindung der Formel II, einem N-Oxid oder einem Salz davon
    worin
    • jedes J unabhängig einen Phenylring oder einen 5- oder 6-gliedrigen heteroaromatischen Ring darstellt, wobei jeder Ring mit 1 bis 4 R5 substituiert ist;
    • A und B unabhängig O oder S darstellen;
    • n für 0, für 1, für 2 oder für 3 steht;
    • R1 für H, C2-C6-Alkylcarbonyl, C2-C6-Alkoxycarbonyl, C2-C6-Alkylaminocarbonyl oder C3-C8-Dialkylaminocarbonyl steht; oder
    • R1 für C1-C6-Alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl oder C3-C6-Cycloalkyl steht, wobei jedes optional mit einem oder mehr Substituenten substituiert ist, die aus der Gruppe ausgewählt sind, bestehend aus Halogen, CN, NO2, Hydroxy, C1-C4-Alkoxy, C1-C4-Alkylthio, C1-C4-Alkylsulfinyl, C1-C4-Alkylsulfonyl, C2-C4-Alkoxycarbonyl, C1-C4-Alkylamino, C2-C8-Dialkylamino und C3-C6-Cycloalkylamino;
    • R2 für H, C1-C6-Alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy, C1-C4-Alkylamino, C2-C8-Dialkylamino, C3-C6-Cycloalkylamino, C2-C6-Alkoxycarbonyl oder C2-C6-Alkylcarbonyl steht;
    • R3 für H steht; oder
    • R3 für C1-C6-Alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl oder C3-C6-Cycloalkyl steht, wobei jedes optional mit einem oder mehr Substituenten substituiert ist, die aus der Gruppe ausgewählt sind, bestehend aus Halogen, CN, NO2, Hydroxy, C1-C4-Alkoxy, C1-C4-Alkylthio, C1-C4-Alkylsulfinyl und C1-C4-Alkylsulfonyl; oder
    • R2 und R3 mit dem Stickstoff zusammen genommen werden können, an den sie zur Bildung eines Rings, enthaltend 2 bis 6 Kohlenstoffatome und optional ein zusätzliches Stickstoff-, Schwefel- oder Sauerstoffatom, gebunden sind, wobei der Ring optional mit 1 bis 4 Substituenten substituiert sein kann, die aus der Gruppe ausgewählt sind, bestehend aus C1-C2-Alkyl, Halogen, CN, NO2 und C1-C2-Alkoxy; und
    • jedes R4 und jedes R5 unabhängig H, C1-C6-Alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, C3-C6-Cycloalkyl, C1-C6-Haloalkyl, C2-C6-Haloalkenyl, C2-C6-Haloalkinyl, C3-C6-Halocycloalkyl, Halogen, CN, CO2H, CONH2, NO2, Hydroxy, C1-C4-Alkoxy, C1-C4-Haloalkoxy, C1-C4-Alkylthio, C1-C4-Alkylsulfinyl, C1-C4-Alkylsulfonyl, C1-C4-Haloalkylthio, C1-C4-Haloalkylsulfinyl, C1-C4-Haloalkylsulfonyl, C1-C4-Alkylamino, C2-C8-Dialkylamino, C3-C6-Cycloalkylamino, C2-C6-Alkylcarbonyl, C2-C6-Alkoxycarbonyl, C2-C6-Alkylaminocarbonyl, C3-C8-Dialkylaminocarbonyl oder C3-C6-Trialkylsilyl darstellt; oder
    • jedes R4 und jedes R5 unabhängig ein Phenyl, Benzyl, Phenoxy oder einen 5- oder 6-gliedrigen heteroaromatischen Ring darstellt, wobei jeder Ring optional mit einem bis drei Substituenten substituiert ist, die unabhängig aus der Gruppe ausgewählt sind, bestehend aus C1-C4-Alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C1-C4-Haloalkyl, C2-C4-Haloalkenyl, C2-C4-Haloalkinyl, C3-C6-Halocycloalkyl, Halogen, CN, NO2, C1-C4-Alkoxy, C1-C4-Haloalkoxy, C1-C4-Alkylthio, C1-C4-Alkylsulfinyl, C1-C4-Alkylsulfonyl, C1-C4-Alkylamino, C2-C8-Dialkylamino, C3-C6-Cycloalkylamino, C3-C6-(Alkyl)cycloalkylamino, C2-C4-Alkylcarbonyl, C2-C6-Alkoxycarbonyl, C2-C6-Alkylaminocarbonyl, C3-C8-Dialkylaminocarbonyl oder C3-C6-Trialkylsilyl; oder
    • zwei R5-Gruppen, wenn sie an benachbarte Kohlenstoffatome gebunden sind, zusammen genommen werden können als -OCF2O-, -CF2CF2O- oder -OCF2CF2O-;
    • M und M1 jeweils unabhängig CR6R7, NR8, O oder S darstellen, wenn die Bindung zwischen M und M1 eine Einfachbindung darstellt; und jeweils unabhängig CR6 oder N darstellen, wenn die Bindung zwischen M und M1 eine aromatische Bindung darstellt;
    • jedes R6 und jedes R7 unabhängig H, C1-C4-Alkyl, Halogen, CN, C1-C4-Haloalkyl oder C1-C4-Alkoxy darstellt; und
    • jedes R8 unabhängig H oder C1-C4-Alkyl darstellt.
  2. Verfahren nach Anspruch 1, umfassend die Applikation einer biologisch wirksamen Menge einer Verbindung der Formel I, worin
    • A und B beide O darstellen;
    • R1 für H, C1-C4-Alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C2-C6-Alkylcarbonyl oder C2-C6-Alkoxycarbonyl steht; und
    • n für 0, für 1 oder für 2 steht.
  3. Verfahren nach Anspruch 1, umfassend die Applikation einer biologisch wirksamen Menge einer Verbindung der Formula II, worin
    • A und B beide O darstellen;
    • R1 für H, C1-C4-Alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C2-C6-Alkylcarbonyl oder C2-C6-Alkoxycarbonyl steht; und
    • n für 0, für 1 oder für 2 steht.
  4. Zusammensetzung, umfassend: mindestens eine Verbindung, die aus der Gruppe ausgewählt ist, bestehend aus einer Verbindung der Formel I wie nach Anspruch 1 definiert, einem N-Oxid oder einem Salz davon, und einer Verbindung der Formel II wie nach Anspruch 1 definiert, einem N-Oxid oder einem Salz davon; und mindestens einer anderen biologisch aktiven Verbindung oder einem anderen biologisch aktiven Mittel.
  5. Zusammensetzung nach Anspruch 4 weiter umfassend eine zusätzliche Komponente, die aus der Gruppe ausgewählt ist, bestehend aus einem Tensid, einem festen Verdünnungsmittel und einem flüssigen Verdünnungsmittel.
  6. Zusammensetzung nach Anspruch 4, worin die andere biologisch aktive Verbindung oder das andere biologisch aktive Mittel aus der Gruppe ausgewählt ist, bestehend aus einem anderen Insektizid, einem Fungizid, einem Nematizid, einem Bakterizid, einem Akarizid, einem Wachstumsregulator, einem Wurzelstimulans, einem Chemosterilans, einer Semiochemikalie, einem Repellens, einem Attraktans, einem Pheromon, einem Fraßstimulans und einem entomopathogenen Bakterium, Virus oder Pilz.
  7. Zusammensetzung nach Anspruch 6, worin das andere Insektizid aus der Gruppe ausgewählt ist, bestehend aus einem Pyrethroid, einem Carbamat, einem Neonicotinoid, einem neuronalen Natriumkanalblocker, einem insektiziden makrocyclischen Lacton, einem γ-Aminobuttersäure-Antagonist (GABA-Antagonist), einem insektiziden Harnstoff, einem Juvenilhormon-Mimik, Pymetrozin und Amitraz.
  8. Zusammensetzung nach Anspruch 6, worin das andere Insektizid aus der Gruppe ausgewählt ist, bestehend aus Abamectin, Acephat, Acetamiprid, Avermectin, Azadirachtin, Azinphos-Methyl, Bifenthrin, Binfenazat, Buprofezin, Carbofuran, Chlorfenapyr, Chlorfluazuron, Chlorpyrifos, Chlorpyrifos-Methyl, Chromafenozid, Clothianidin, Cyfluthrin, β-Cyfluthrin, Cyhalothrin, λ-Cyhalothrin, Cypermethrin, Cyromazin, Deltamethrin, Diafenthiuron, Diazinon, Diflubenzuron, Dimethoat, Diofenolan, Emamectin, Endosulfan, Esfenvalerat, Ethiprol, Fenothicarb, Fenoxycarb, Fenpropathrin, Fenproximat, Fenvalerat, Fipronil, Flonicamid, Flucythrinat, τ-Fluvalinat, Flufenoxuron, Fonophos, Halofenozid, Hexaflumuron, Imidacloprid, Indoxacarb, Isofenphos, Lufenuron, Malathion, Metaldehyd, Methamidophos, Methidathion, Methomyl, Methopren, Methoxychlor, Monocrotophos, Methoxyfenozid, Nithiazin, Novaluron, Oxamyl, Parathion, Parathion-Methyl, Permethrin, Phorat, Phosalon, Phosmet, Phosphamidon, Pirimicarb, Profenofos, Pymetrozin, Pyridalyl, Pyriproxyfen, Rotenon, Spinosad, Sulprofos, Tebufenozid, Teflubenzuron, Tefluthrin, Terbufos, Tetrachlorvinphos, Thiacloprid, Thiamethoxam, Thiodicarb, Thiosultap-Natrium, Tralomethrin, Trichlorfon und Triflumuron, Aldicarb, Oxamyl, Fenamiphos, Amitraz, Chinomethionat, Chlorobenzilat, Cyhexatin, Dicofol, Dienochlor, Etoxazol, Fenazaquin, Fenbutatinoxid, Fenpropathrin, Fenpyroximat, Hexythiazox, Propargit, Pyridaben, Tebufenpyrad, Bacillus thuringiensis, δ-Endotoxin von Bacillus thuringiensis, Baculovirus und entomopathogenen Bakterien, Viren und Pilzen.
  9. Zusammensetzung nach Anspruch 6, worin das andere Insektizid aus der Gruppe ausgewählt ist, bestehend aus Cypermethrin, Cyhalothrin, Cyfluthrin, β-Cyfluthrin, Esfenvalerat, Fenvalerat, Tralomethrin, Fenothicarb, Methomyl, Oxamyl, Thiodicarb, Clothianidin, Imidacloprid, Thiacloprid, Indoxacarb, Spinosad, Abamectin, Avermectin, Emamectin, Endosulfan, Ethiprol, Fipronil, Flufenoxuron, Triflumuron, Diofenolan, Pyriproxyfen, Pymetrozin, Amitraz, Bacillus thuringiensis, δ-Endotoxin von Bacillus thuringiensis und entomophagen Pilzen.
  10. Verfahren zur Kontrolle von mindestens einem wirbellosen Schädling, umfassend:
    • Kontaktieren des wirbellosen Schädlings oder seiner Umgebung mit einer biologisch wirksamen Menge einer Zusammensetzung nach Anspruch 4 oder 5.
  11. Verbindung der Formel II wie nach Anspruch 1 definiert, ein N-Oxid davon oder ein Salz davon.
  12. Verbindung nach Anspruch 11, worin
    • A und B beide O darstellen;
    • R1 für H, C1-C4-Alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C2-C6-Alkylcarbonyl oder C2-C6-Alkoxycarbonyl steht; und
    • n für 0, für 1 oder für 2 steht.
  13. Verbindung nach Anspruch 12, worin
    • J einen Phenylring oder einen 5- oder 6-gliedrigen heteroaromatischen Ring darstellt, der aus der Gruppe ausgewählt ist, bestehend aus J-1, J-2, J-3 und J-4, wobei jeder J-Ring optional mit 1 bis 3 R5 substituiert ist
    • Q für O, S oder NR5 steht;
    • W, X, Y und Z unabhängig N oder CR5 darstellen, vorausgesetzt, dass in J-3 und J-4 mindestens eine der Gruppen aus W, X, Y besteht und Z für N steht;
    • R2 für H, C1-C4-Alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C2-C6-Alkylcarbonyl oder C2-C6-Alkoxycarbonyl steht;
    • R3 für H, C1-C6-Alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl oder C3-C6-Cycloalkyl steht, wobei jedes optional mit einem oder mehr Substituenten substituiert ist, die aus der Gruppe ausgewählt sind, bestehend aus Halogen, CN, C1-C2-Alkoxy, C1-C2-Alkylthio, C1-C2-Alkylsulfinyl und C1-C2-Alkylsulfonyl;
    • jedes R4 unabhängig C1-C4-Alkyl, C1-C4-Haloalkyl, Halogen, CN, NO2, C1-C4-Alkoxy, C1-C4-Haloalkoxy, C1-C4-Alkylthio, C1-C4-Alkylsulfinyl, C1-C4-Alkylsulfonyl, C1-C4-Haloalkylthio, C1-C4-Haloalkylsulfinyl oder C1-C4-Haloalkylsulfonyl darstellt;
    • jedes R5 unabhängig H, C1-C4-Alkyl, C1-C6-Haloalkyl, Halogen, CN, NO2, C1-C4-Alkoxy, C1-C4-Haloalkoxy, C1-C4-Alkylthio, C1-C4-Alkylsulfinyl, C1-C4-Alkylsulfonyl, C 1-C4-Haloalkylthio; C1-C4-Haloalkylsulfinyl, C1-C4-Haloalkylsulfonyl oder C2-C4-Alkoxycarbonyl, C2-C6-Alkylaminocarbonyl, C3-C8-Dialkylaminocarbonyl darstellt; oder
    • jedes R5 unabhängig ein Phenyl, Benzyl oder einen 5- oder 6-gliedrigen heteroaromatischen Ring darstellt, wobei jeder Ring optional substituiert ist mit: C1-C4-Alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C1-C4-Haloalkyl, C2-C4-Haloalkenyl, C2-C4-Haloalkinyl, C3-C6-Halocycloalkyl, Halogen, CN, NO2, C1-C4-Alkoxy, C1-C4-Haloalkoxy, C1-C4-Alkylthio, C1-C4-Alkylsulfinyl, C1-C4-Alkylsulfonyl, C1-C4-Alkylamino, C2-C8-Dialkylamino, C3-C6-Cycloalkylamino, C3-C6-(Alkyl)cycloalkylamino, C2-C4-Alkylcarbonyl, C2-C6-Alkoxycarbonyl, C2-C6-Alkylaminocarbonyl, C3-C8-Dialkylaminocarbonyl oder C3-C6-Trialkylsilyl; oder
    • zwei R5-Gruppen, wenn sie an benachbarte Kohlenstoffatome gebunden sind, zusammengenommen werden können als -OCF2O-, -CF2CF2O- oder -OCF2CF2O-.
  14. Verbindung nach Anspruch 13, worin
    • R2 für H steht;
    • R3 für C1-C4-Alkyl steht; und
    • mindestens ein R5 anders als H ist und an J an der ortho-Stellumg an die N(R1)C(=B)-Komponente gebunden ist.
  15. Zusammensetzung, umfassend:
    • mindestens eine Verbindung nach Anspruch 11; und
    • mindestens eine zusätzliche Komponente, die aus der Gruppe ausgewählt ist, bestehend aus einem Tensid, einem festen Verdünnungsmittel, einem flüssigen Verdünnungsmittel und einer anderen biologisch aktiven Verbindung oder einem anderen biologisch aktiven Mittel.
  16. Verfahren zur Kontrolle von mindestens einem wirbellosen Schädling, umfassend: Kontaktieren des wirbellosen Schädlings oder seiner Umgebung mit einer biologisch wirksamen Menge einer Verbindung nach Anspruch 11 oder mit einer biologisch wirksamen Menge einer Zusammensetzung nach Anspruch 15.
  17. Verbindung der Formula Id, eines N-Oxids oder eines Salzes davon,
    worin
    • jedes J unabhängig einen Phenylring oder einen 5- oder 6-gliedrigen heteroaromatischen Ring darstellt, wobei jeder Ring optional mit 1 bis 4 R5 substituiert ist;
    • A und B unabhängig O oder S darstellen;
    • n für 0, für 1, für 2 oder für 3 steht;
    • R1 für H, C2-C6-Alkylcarbonyl, C2-C6-Alkoxycarbonyl, C2-C6-Akylaminocarbonyl oder C3-C8-Dialkylaminocarbonyl steht; oder
    • R1 für C1-C6-Alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl oder C3-C6-Cycloalkyl steht, wobei jedes optional mit einem oder mehr Substituenten substituiert ist, die aus der Gruppe ausgewählt sind, bestehend aus Halogen, CN, NO2, Hydroxy, C1-C4-Alkoxy, C1-C4-Alkylthio, C1-C4-Alkylsulfinyl, C1-C4-Alkylsulfonyl, C2-C4-Alkoxycarbonyl, C1-C4-Alkylamino, C2-C8-Dialkylamino und C3-C6-Cycloalkylamino;
    • R2 für H, C1-C6-Alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, C3-C6-Cycloalkyl, C1-C4-Alkoxy, C1-C4-Alkylamino, C2-C8-Dialkylamino, C3-C6-Cycloalkylamino, C2-C6-Alkoxycarbonyl oder C2-C6-Alkylcarbonyl steht;
    • R3 für H steht; oder
    • R3 für C1-C6-Alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl oder C3-C6-Cycloalkyl steht, wobei jedes optional mit einem oder mehr Substituenten substituiert ist, die aus der Gruppe ausgewählt sind, bestehend aus Halogen, CN, NO2, Hydroxy, C1-C4-Alkoxy, C1-C4-Alkylthio, C1-C4-Alkylsulfinyl und C1-C4-Alkylsulfonyl; oder
    • R2 und R3 mit dem Stickstoff zusammengenommen werden können, an den sie zur Bildung eines Rings, enthaltend 2 bis 6 Kohlenstoffatome und optional ein zusätzliches Stickstoff-, Schwefel- oder Sauerstoffatom gebunden sind, wobei der Ring optional mit 1 bis 4 Substituenten substituiert sein kann, die aus der Gruppe ausgewählt sind, bestehend aus C1-C2-Alkyl, Halogen, CN, NO2 und C1-C2-Alkoxy; und
    • jedes R4 und jedes R5 unabhängig H, C1-C6-Alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, C3-C6-Cycloalkyl, C1-C6-Haloalkyl, C2-C6-Haloalkenyl, C2-C6-Haloalkinyl, C3-C6-Halocycloalkyl, Halogen, CN, CO2H, CONH2, NO2, Hydroxy, C1-C4-Alkoxy, C1-C4-Haloalkoxy, C1-C4-Alkylthio, C1-C4-Alkylsulfinyl, C1-C4-Alkylsulfonyl, C1-C4-Haloalkylthio, C1-C4-Haloalkylsulfinyl, C1-C4-Haloalkylsulfonyl, C1-C4-Alkylamino, C2-C8-Dialkylamino, C3-C6-Cycloalkylamino, C2-C6-Alkylcarbonyl, C2-C6-Alkoxycarbonyl, C2-C6-Alkylaminocarbonyl, C3-C8-Dialkylaminocarbonyl oder C3-C6-Trialkylsilyl darstellt; oder
    • jedes R5 unabhängig ein Phenyl, Benzyl, Phenoxy oder einen 5- oder 6-gliedrigen heteroaromatischen Ring darstellt, wobei jeder Ring optional mit einem bis drei Substituenten optional substituiert ist, die unabhängig aus der Gruppe ausgewählt sind, bestehend aus C1-C4-Alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C1-C4-Haloalkyl, C2-C4-Haloalkenyl, C2-C4-Haloalkinyl, C3-C6-Halocycloalkyl, Halogen, CN, NO2, C1-C4-Alkoxy, C1-C4-Haloalkoxy, C1-C4-Alkylthio, C1-C4-Alkylsulfinyl, C1-C4-Alkylsulfonyl, C1-C4-Alkylamino, C2-C8-Dialkylamino, C3-C6-Cycloalkylamino, C3-C6-(Alkyl)cycloalkylamino, C2-C4-Alkylcarbonyl, C2-C6-Alkoxycarbonyl, C2-C6-Alkylaminocarbonyl, C3-C8-Dialkylaminocarbonyl oder C3-C6-Trialkylsilyl; oder
    • zwei R5-Gruppen, wenn sie an benachbarte Kohlenstoffatome gebunden sind, zusammengenommen werden können als -OCF2O-, -CF2CF2O- oder -OCF2CF2O-;
    • M und M1 jeweils unabhängig CR6R7, NR8, O oder S darstellen, wenn die Bindung zwischen M und M1 eine Einfachbindung darstellt; und jeweils unabhängig CR6 oder N darstellen, wenn die Bindung zwischen M und M1 eine aromatische Bindung darstellt;
    • jedes R6 und jedes R7 unabhängig H, C1-C4-Alkyl, Halogen, CN, C1-C4-Haloalkyl oder C1-C4-Alkoxy darstellt; und
    • jedes R8 unabhängig H oder C1-C4-Alkyl darstellt.
  18. Verbindung nach Anspruch 17, worin
    • A und B beide O darstellen;
    • R1 für H, C1-C4-Alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C2-C6-Alkylcarbonyl oder C2-C6-Alkoxycarbonyl steht; und
    • n für 0, für 1 oder für 2 steht.
  19. Verbindung nach Anspruch 18, worin
    • J einen Phenylring oder einen 5- oder 6-gliedrigen heteroaromatischen Ring darstellt, der aus der Gruppe ausgewählt ist, bestehend aus J-1, J-2, J-3 und J-4
    • Q für O, S oder NR5 steht;
    • W, X, Y und Z unabhängig N oder CR5 darstellen, vorausgesetzt, dass in J-3 und J-4 mindestens eine der Gruppen aus W, X, Y besteht und Z für N steht;
    • R2 für H, C1-C4-Alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C2-C6-Alkylcarbonyl oder C2-C6-Alkoxycarbonyl steht;
    • R3 für H, C1-C6-Alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl oder C3-C6-Cycloalkyl steht, wobei jedes optional mit einem oder mehr Substituenten substituiert ist, die aus der Gruppe ausgewählt sind, bestehend aus Halogen, CN, C1-C2-Alkoxy, C1-C2-Alkylthio, C1-C2-Alkylsulfinyl und C1-C2-Alkylsulfonyl;
    • jedes R4 unabhängig C1-C4-Alkyl, C1-C4-Haloalkyl, Halogen, CN, NO2, C1-C4-Alkoxy, C1-C4-Haloalkoxy, C1-C4-Alkylthio, C1-C4-Alkylsulfinyl, C1-C4-Alkylsulfonyl, C1-C4-Haloalkylthio, C1-C4-Haloalkylsulfinyl oder C1-C4-Haloalkylsulfonyl darstellt;
    • jedes R5 unabhängig H, C1-C4-Alkyl, C1-C6-Haloalkyl, Halogen, CN, NO2, C1-C4-Alkoxy, C1-C4-Haloalkoxy, C1-C4-Alkylthio, C1-C4-Alkylsulfinyl, C1-C4-Alkylsulfonyl, C1-C4-Haloalkylthio, C1-C4-Haloalkylsulfinyl, C1-C4-Haloalkylsulfonyl oder C2-C4-Alkoxycarbonyl, C2-C6-Alkylaminocarbonyl, C3-C8-Dialkylaminocarbonyl darstellt; oder
    • jedes R5 unabhängig ein Phenyl, Benzyl oder einen 5- oder 6-gliedrigen heteroaromatischen Ring darstellt, wobei jeder Ring optional substituiert ist mit: C1-C4-Alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C1-C4-Haloalkyl, C2-C4-Haloalkenyl, C2-C4-Haloalkinyl, C3-C6-Halocycloalkyl, Halogen, CN, NO2, C1-C4-Alkoxy, C1-C4-Haloalkoxy, C1-C4-Alkylthio, C1-C4-Alkylsulfinyl, C1-C4-Alkylsulfonyl, C1-C4-Alkylamino, C2-C8-Dialkylamino, C3-C6-Cycloalkylamino, C3-C6-(Alkyl)cycloalkylamino, C2-C4-Alkylcarbonyl, C2-C6-Alkoxycarbonyl, C2-C6-Alkylaminocarbonyl, C3-C8-Dialkylaminocarbonyl oder C3-C6-Trialkylsilyl; oder
    • zwei R5-Gruppen, wenn sie an benachbarte Kohlenstoffatome gebunden sind, zusammengenommen werden können als -OCF2O-, -CF2CF2O- oder -OCF2CF2O-.
  20. Verbindung nach Anspruch 19, worin
    • R1 für H oder C1-C4-Alkyl steht;
    • R2 für H oder C1-C4-Alkyl steht;
    • R3 für H, C1-C4-Alkyl optional substituiert mit Halogen, CN, OCH3, oder S(O)pCH3 steht;
    • jedes R5 unabhängig H, C1-C4-Alkyl, C1-C4-Haloalkyl, Halogen, CN, NO2, C1-C4-Alkoxy, C1-C4-Haloalkoxy, C1-C4-Alkylthio, C1-C4-Alkylsulfinyl, C1-C4-Alkylsulfonyl, C1-C4-Haloalkylthio, C1-C4-Haloalkylsulfinyl, C1-C4-Haloalkylsulfonyl, C2-C4-Alkoxycarbonyl oder C3-C8-Dialkylaminocarbonyl; oder ein Phenyl, Benzyl, oder einen 5- oder 6-gliedrigen heteroaromatischen Ring darstellt, wobei jeder Ring optional substituiert ist mit Halogen, CN, NO2, C1-C4-Alkyl, C2-C4-Alkenyl, C2-C4-Alkinyl, C3-C6-Cycloalkyl, C1-C4-Haloalkyl, C1-C4-Alkoxy oder C1-C4-Haloalkoxy;
    • vorausgesetzt, dass mindestens ein R5 anders als H ist und an J an der ortho-Stellung an die N(R1)C(=B)-Komponente gebunden ist; und
    • p für 0, für 1 oder für 2 steht.
  21. Verbindung nach Anspruch 20, worin
    • J ein substituiertes Phenyl, ein substituiertes Pyrazol, ein substituiertes Pyrrol, ein substituiertes Pyridin oder ein substituiertes Pyrimidin darstellt.
  22. Verbindung nach Anspruch 21, worin R1 und R2 jeweils H darstellen.
  23. Zusammensetzung, umfassend: mindestens eine Verbindung nach Anspruch 17; und mindestens eine zusätzliche Komponente, die aus der Gruppe ausgewählt ist, bestehend aus einem Tensid, einem festen Verdünnungsmittel, einem flüssigen Verdünnungsmittel und einer anderen biologisch aktiven Verbindung oder einem anderen biologisch aktiven Mittel.
  24. Verfahren zur Kontrolle von mindestens einem wirbellosen Schädling, umfassend: Kontaktieren des wirbellosen Schädlings oder seiner Umgebung mit einer biologisch wirksamen Menge einer Verbindung nach Anspruch 17 oder mit einer biologisch wirksamen Menge einer Zusammensetzung nach Anspruch 23.
Anspruch[en]
  1. A method for controlling at least one invertebrate pest, comprising: contacting the invertebrate pest or its environment with a biologically effective amount of at least one compound selected from the group consisting of a compound of Formula I, an N-oxide or a salt thereof, and a compound of Formula II, an N-oxide or a salt thereof
       wherein
    each J
    is independently a phenyl ring or a 5- or 6-membered heteroaromatic ring, each ring substituted with 1 to 4 R5;
    A and B
    are independently O or S;
    n
    is 0, 1, 2 or 3;
    R1
    is H, C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl or C3-C8 dialkylaminocarbonyl; or
    R1
    is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C3-C6 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO2, hydroxy, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C2-C4 alkoxycarbonyl, C1-C4 alkylamino, C2-C8 dialkylamino and C3-C6 cycloalkylamino;
    R2
    is H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C4 alkoxy, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkoxycarbonyl or C2-C6 alkylcarbonyl;
    R3
    is H; or
    R3
    is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C3-C6 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO2, hydroxy, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl and C1-C4 alkylsulfonyl; 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 C1-C2 alkyl, halogen, CN, NO2 and C1-C2 alkoxy; and
    each R4 and each R5
    is independently H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, CO2H, CONH2, NO2, hydroxy, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl, or C3-C6 trialkylsilyl; or
    each R4 and each R5
    is independently a phenyl, benzyl, phenoxy, or 5- or 6-membered heteroaromatic ring, each ring optionally substituted with one to three substituents independently selected from the group consisting of C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, NO2, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C3-C6 (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl or C3-C6 trialkylsilyl; or
    two R5
    groups when attached to adjacent carbon atoms can be taken together as -OCF2O-, -CF2CF2O- or -OCF2CF2O-;
    M and M1
    are each independently CR6R7, NR8, O or S when the bond between M and M1 is a single bond; and are each independently CR6 or N when the bond between M and M1 is an aromatic bond;
    each R6 and each R7
    is independently H, C1-C4 alkyl, halogen, CN, C1-C4 haloalkyl or C1-C4 alkoxy; and
    each R8
    is independently H or C1-C4 alkyl.
  2. The method of Claim 1 comprising applying a biologically effective amount of a compound of Formula I wherein
    A and B
    are both O;
    R1
    is H, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C2-C6 alkylcarbonyl or C2-C6 alkoxycarbonyl; and
    n
    is 0, 1 or 2.
  3. The method of Claim 1 comprising applying a biologically effective amount of a compound of Formula II wherein
    A and B
    are both O;
    R1
    is H, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C2-C6 alkylcarbonyl or C2-C6 alkoxycarbonyl; and
    n
    is 0, 1 or 2.
  4. A composition comprising: at least one compound selected from the group consisting of a compound of Formula I as defined in Claim 1, an N-oxide or a salt thereof, and a compound of Formula II as defined in Claim 1, an N-oxide or a salt thereof; and at least one other biologically active compound or agent.
  5. The composition of Claim 4 further comprising an additional component selected from the group consisting of a surfactant, a solid diluent, and a liquid diluent.
  6. The composition of Claim 4 wherein the other biologically active compound or agent is selected from the group consisting of an other insecticide, a fungicide, a nematocide, a bactericide, an acaricide, a growth regulator, a rooting stimulant, a chemosterilant, a semiochemical, a repellent, an attractant, a pheromone, a feeding stimulant, and a entomopathogenic bacterium, virus or fungus.
  7. The composition of Claim 6 wherein the other insecticide is selected from the group consisting of a pyrethroid, a carbamate, a neonicotinoid, a neuronal sodium channel blocker, an insecticidal macrocyclic lactone, a γ-aminobutyric acid (GABA) antagonist, an insecticidal urea, a juvenile hormone mimic, pymetrozine, and amitraz.
  8. The composition of Claim 6 wherein the other insecticide is selected from the group consisting of abamectin, acephate, acetamiprid, avermectin, azadirachtin, azinphos-methyl, bifenthrin, binfenazate, buprofezin, carbofuran, chlorfenapyr, chlorfluazuron, chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clothianidin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, cypermethrin, cyromazine, deltamethrin, diafenthiuron, diazinon, diflubenzuron, dimethoate, diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, fenothicarb, fenoxycarb, fenpropathrin, fenproximate, fenvalerate, fipronil, flonicamid, flucythrinate, tau-fluvalinate, flufenoxuron, fonophos, halofenozide, hexaflumuron, imidacloprid, indoxacarb, isofenphos, lufenuron, malathion, metaldehyde, methamidophos, methidathion, methomyl, methoprene, methoxychlor, monocrotophos, methoxyfenozide, nithiazin, novaluron, oxamyl, parathion, parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, pymetrozine, pyridalyl, pyriproxyfen, rotenone, spinosad, sulprofos, tebufenozide, teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tralomethrin, trichlorfon and triflumuron, aldicarb, oxamyl, fenamiphos, amitraz, chinomethionat, chlorobenzilate, cyhexatin, dicofol, dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpropathrin, fenpyroximate, hexythiazox, propargite, pyridaben, tebufenpyrad, Bacillus thuringiensis, Bacillus thuringiensis delta endotoxin, baculovirus, and entomopathogenic bacteria, virus and fungi.
  9. The composition of Claim 6 wherein the other insecticide is selected from the group consisting of cypermethrin, cyhalothrin, cyfluthrin, beta-cyfluthrin, esfenvalerate, fenvalerate, tralomethrin, fenothicarb, methomyl, oxamyl, thiodicarb, clothianidin, imidacloprid, thiacloprid, indoxacarb, spinosad, abamectin, avermectin, emamectin, endosulfan, ethiprole, fipronil, flufenoxuron, triflumuron, diofenolan, pyriproxyfen, pymetrozine, amitraz, Bacillus thuringiensis, Bacillus thuringiensis delta endotoxin and entomophagous fungi.
  10. A method for controlling at least one invertebrate pest, comprising:
    • contacting the invertebrate pest or its environment with a biologically effective amount of a composition of Claim 4 or Claim 5.
  11. A compound of Formula II as defined in Claim 1, an N-oxide thereof or a salt thereof.
  12. The compound of Claim 11 wherein
    A and B
    are both O;
    R1
    is H, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C2-C6 alkylcarbonyl or C2-C6 alkoxycarbonyl; and
    n
    is 0, 1 or 2.
  13. The compound of Claim 12 wherein
    J
    is a phenyl ring or a 5- or 6-membered heteroaromatic ring selected from the group consisting of J-1, J-2, J-3 and J-4, each J ring optionally substituted with 1 to 3 R5
    Q
    is O, S or NR5;
    W, X, Y and Z
    are independently N or CR5, provided that in J-3 and J-4 at least one of the group consisting of W, X, Y and Z is N;
    R2
    is H, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C2-C6 alkylcarbonyl or C2-C6 alkoxycarbonyl;
    R3
    is H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C3-C6 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, C1-C2 alkoxy, C1-C2 alkylthio, C1-C2 alkylsulfinyl and C1-C2 alkylsulfonyl;
    each R4
    is independently C1-C4 alkyl, C1-C4 haloalkyl, halogen, CN, NO2, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl or C1-C4 haloalkylsulfonyl;
    each R5
    is independently H, C1-C4 alkyl, C1-C6 haloalkyl, halogen, CN, NO2, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl or C2-C4 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl; or
    each R5
    is independently a phenyl, benzyl or a 5- or 6-membered heteroaromatic ring, each ring optionally substituted with C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, NO2, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C3-C6 (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl or C3-C6 trialkylsilyl; or
    two R5
    groups when attached to adjacent carbon atoms can be taken together as -OCF2O-, -CF2CF2O- or -OCF2CF2O-.
  14. The compound of Claim 13 wherein
    R2
    is H;
    R3
    is C1-C4 alkyl; and
    at least one R5 is other than H and is attached to J at the position ortho to the N(R1)C(=B) moiety.
  15. A composition comprising:
    • at least one compound of Claim 11; and
    • at least one additional component selected from the group consisting of a surfactant, a solid diluent, a liquid diluent and an other biologically active compound or agent.
  16. A method for controlling at least one invertebrate pest, comprising: contacting the invertebrate pest or its environment with a biologically effective amount of a compound of Claim 11 or with a biologically effective amount of a composition of Claim 15.
  17. A compound of Formula Id, an N-oxide or a salt thereof,
       wherein
    each J
    is independently a phenyl ring or a 5- or 6-membered heteroaromatic ring, each ring optionally substituted with 1 to 4 R5;
    A and B
    are independently O or S;
    n
    is 0, 1, 2 or 3;
    R1
    is H, C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl or C3-C8 dialkylaminocarbonyl; or
    R1
    is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C3-C6 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO2, hydroxy, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C2-C4 alkoxycarbonyl, C1-C4 alkylamino, C2-C8 dialkylamino and C3-C6 cycloalkylamino;
    R2
    is H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C4 alkoxy, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkoxycarbonyl or C2-C6 alkylcarbonyl;
    R3
    is H; or
    R3
    is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C3-C6 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO2, hydroxy, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl and C1-C4 alkylsulfonyl; 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 C1-C2 alkyl, halogen, CN, NO2 and C1-C2 alkoxy; and
    each R4 and each R5
    is independently H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, CO2H, CONH2, NO2, hydroxy, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl, or C3-C6 trialkylsilyl; or
    each R5
    is independently a phenyl, benzyl, phenoxy, or 5- or 6-membered heteroaromatic ring, each ring optionally substituted with one to three substituents independently selected from the group consisting of C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, NO2, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C3-C6 (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl or C3-C6 trialkylsilyl; or
    two R5
    groups when attached to adjacent carbon atoms can be taken together as -OCF2O-, -CF2CF2O- or -OCF2CF2O-;
    M and M1
    are each independently CR6R7, NR8, O or S when the bond between M and M1 is a single bond; and are each independently CR6 or N when the bond between M and M1 is an aromatic bond;
    each R6 and each R7
    is independently H, C1-C4 alkyl, halogen, CN, C1-C4 haloalkyl or C1-C4 alkoxy; and
    each R8
    is independently H or C1-C4 alkyl.
  18. The compound of Claim 17 wherein
    A and B
    are both O;
    R1
    is H, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C2-C6 alkylcarbonyl or C2-C6 alkoxycarbonyl; and
    n
    is 0, 1 or 2.
  19. The compound of Claim 18 wherein
    J
    is a phenyl ring or a 5- or 6-membered heteroaromatic ring selected from the group consisting of J-1, J-2, J-3 and J-4
    Q
    is O, S or NR5;
    W, X, Y and Z
    are independently N or CR5, provided that in J-3 and J-4 at least one of the group consisting of W, X, Y and Z is N;
    R2
    is H, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C2-C6 alkylcarbonyl or C2-C6 alkoxycarbonyl;
    R3
    is H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C3-C6 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, C1-C2 alkoxy, C1-C2 alkylthio, C1-C2 alkylsulfinyl and C1-C2 alkylsulfonyl;
    each R4
    is independently C1-C4 alkyl, C1-C4 haloalkyl, halogen, CN, NO2, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl or C1-C4 haloalkylsulfonyl;
    each R5
    is independently H, C1-C4 alkyl, C1-C6 haloalkyl, halogen, CN, NO2, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl or C2-C4 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl; or
    each R5
    is independently a phenyl, benzyl or a 5- or 6-membered heteroaromatic ring, each ring optionally substituted with C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, NO2, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C3-C6 (alkyl)cycloalkylamino, C2-C4 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl or C3-C6 trialkylsilyl; or
    two R5
    groups when attached to adjacent carbon atoms can be taken together as -OCF2O-, -CF2CF2O- or -OCF2CF2O-.
  20. The compound of Claim 19 wherein
    R1
    is H or C1-C4 alkyl;
    R2
    is H or C1-C4 alkyl;
    R3
    is H, C1-C4 alkyl optionally substituted with halogen, CN, OCH3, or S(O)pCH3;
    each R5
    is independently H, C1-C4 alkyl, C1-C4 haloalkyl, halogen, CN, NO2, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, C2-C4 alkoxycarbonyl or C3-C8 dialkylaminocarbonyl; or a phenyl, benzyl, or a 5- or 6-membered heteroaromatic ring, each ring optionally substituted with halogen, CN, NO2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy;

    provided that at least one R5 is other than H and is attached to J at the position ortho to the N(R1)C(=B) moiety; and
    p
    is 0, 1 or 2.
  21. The compound of Claim 20 wherein
    J
    is a substituted phenyl, a substituted pyrazole, a substituted pyrrole, a substituted pyridine or a substituted pyrimidine.
  22. The compound of Claim 21 wherein R1 and R2 are each H.
  23. A composition comprising: at least one compound of Claim 17; and at least one additional component selected from the group consisting of a surfactant, a solid diluent, a liquid diluent and an other biologically active compound or agent.
  24. A method for controlling at least one invertebrate pest, comprising: contacting the invertebrate pest or its environment with a biologically effective amount of a compound of Claim 17 or with a biologically effective amount of a composition of Claim 23.
Anspruch[fr]
  1. Procédé de contrôle d'au moins un animal nuisible invertébré, comprenant: la mise en contact de l'animal nuisible invertébré ou de son environnement avec une quantité biologiquement efficace d'au moins un composé choisi parmi le groupe constitué d'un composé de formule I, un N-oxyde ou un sel de celui-ci, et un composé de formule II, un N-oxyde ou un sel de celui-ci
    dans lesquelles
    • chaque J représente indépendamment un cycle phényle ou un noyau hétéroaromatique à 5 ou 6 chaînons, chaque cycle substitué avec 1 à 4 R5;
    • A et B représentent indépendamment O ou S;
    • n a la valeur de 0, de 1, de 2 ou de 3;
    • R' représente un H, alkylcarbonyle en C2-C6, alcoxycarbonyle en C2-C6, alkylaminocarbonyle en C2-C6 ou dialkylaminocarbonyle en C3-C8; ou
    • R' représente un alkyle en C1-C6, un alcényle en C2-C6, un alcynyle en C2-C6 ou un cycloalkyle en C3-C6 chacun éventuellement substitué avec un ou plusieurs substituant(s) choisi(s) parmi le groupe constitué d'un halogène, CN, NO2, un hydroxy, un alcoxy en C1-C4, un alkylthio en C1-C4, un alkylsulfinyle en C1-C4, un alkylsulfonyle en C1-C4, un alcoxycarbonyle en C2-C4, un alkylamino en C1-C4, un dialkylamino en C2-C8 et un cycloalkylamino en C3-C6;
    • R2 représente H, un alkyle en C1-C6, un alcényle en C2-C6, un alcynyle en C2-C6, un cycloalkyle en C3-C6, un alcoxy en C1-C4, un alkylamino en C1-C4, un dialkylamino en C2-C8, un cycloalkylamino en C3-C6, un alcoxycarbonyle en C2-C6, ou un alkylcarbonyle en C2-C6;
    • R3 représente H; ou
    • R3 représente un alkyle en C1-C6, un alcényle en C2-C6, un alcynyle en C2-C6 ou un cycloalkyle en C3-C6 chacun éventuellement substitué avec un ou plusieurs substituant(s) choisi(s) parmi le groupe constitué d'un halogène, CN, NO2, un hydroxy, un alcoxy en C1-C4, un alkylthio en C1-C4, un alkylsulfinyle en C1-C4 et un alkylsulfonyle en C1-C4; ou
    • R2 et R3 peuvent être pris conjointement avec l'azote auquel ils sont fixés pour former un cycle contenant 2 à 6 atomes de carbone et éventuellement un atome supplémentaire d'azote, de soufre ou d'oxygène, ledit cycle peut être éventuellement substitué avec 1 à 4 substituant(s) choisi(s) parmi le groupe constitué d'un alkyle en C1-C2, un halogène, CN, NO2 et un alcoxy en C1-C2; et
    • chaque R4 et chaque R5 représentent indépendamment H, un alkyle en C1-C6, un alcényle en C2-C6, un alcynyle en C2-C6, un cycloalkyle en C3-C6, un alkyle en C1-C6 halogéné, un alcényle en C2-C6 halogéné, un alcynyle en C2-C6 halogéné, un cycloalkyle en C3-C6 halogéné, un halogène, CN, CO2H, CONH2, NO2, un hydroxy, un alcoxy en C1-C4, un alcoxy en C1-C4 halogéné, un alkylthio en C1-C4, un alkylsulfinyle en C1-C4, un alkylsulfonyle en C1-C4, un alkylthio en C1-C4 halogéné, un alkylsulfinyle en C1-C4 halogéné, un alkylsulfonyle en C1-C4 halogéné, un alkylamino en C1-C4, un dialkylamino en C2-C8, un cycloalkylamino en C3-C6, un alkylcarbonyle en C2-C6, un alcoxycarbonyle en C2-C6, un alkylaminocarbonyle en C2-C6, un dialkylaminocarbonyle en C3-C8, ou un trialkylsilyle en C3-C6; ou
    • chaque R4 et chaque R5 représentent indépendamment un phényle, un benzyle, un phénoxy ou un cycle hétéroaromatique à 5 ou 6 chaînons, chaque cycle éventuellement substitué avec un à trois substituant(s) indépendamment choisi(s) parmi le groupe constitué d'un alkyle en C1-C4, un alcényle en C2-C4, un alcynyle en C2-C4, un cycloalkyle en C3-C6, un alkyle en C1-C4 halogéné, un alcényle en C2-C4 halogéné, un alcynyle en C2-C4 halogéné, un cycloalkyle en C3-C6 halogéné, un halogène, CN, NO2, un alcoxy en C1-C4, un alcoxy en C1-C4 halogéné, un alkylthio en C1-C4, un alkylsulfinyle en C1-C4, un alkylsulfonyle en C1-C4, un alkylamino en C1-C4, un dialkylamino en C2-C8, un cycloalkylamino en C3-C6, un (alkyl)cycloalkylamino en C3-C6, un alkylcarbonyle en C2-C4, un alcoxycarbonyle en C2-C6, un alkylaminocarbonyle en C2-C6, un dialkylaminocarbonyle en C3-C8, ou un trialkylsilyle en C3-C6;

         ou
    • deux groupes R5 lorsque fixés à des atomes de carbone adjacents peuvent être pris conjointement comme -OCF2O-, -CF2CF2O- ou -OCF2CF2O-;
    • M et M1 représentent chacun indépendamment CR6R7, NR8, O ou S lorsque la liaison entre M et M1 est une liaison simple; et représentent chacun indépendamment CR6 ou N lorsque la liaison entre M et M1 est une liaison aromatique;
    • chaque R6 et chaque R7 représentent indépendamment H, un alkyle en C1-C4, un halogène, CN, un alkyle en C1-C4 halogéné ou un alcoxy en C1-C4; et
    • chaque R8 représente indépendamment un atome d'hydrogène ou un groupe alkyle en C1-C4.
  2. Procédé selon la revendication 1, comprenant l'application d'une quantité biologiquement efficace d'un composé de formule I, dans laquelle
    • A et B représentent tous deux un atome O;
    • R1 représente un atome H, un groupe alkyle en C1-C4, alcényle en C2-C4, alcynyle en C2-C4, cycloalkyle en C3-C6, alkylcarbonyle en C2-C6 ou alcoxycarbonyle en C2-C6; et
    • n a la valeur de 0, de 1 ou de 2.
  3. Procédé selon la revendication 1, comprenant l'application d'une quantité biologiquement efficace d'un composé de formule II, dans laquelle
    • A et B représentent tous deux un atome O;
    • R1 représente un atome H, un groupe alkyle en C1-C4, alcényle en C2-C4, alcynyle en C2-C4, cycloalkyle en C3-C6, alkylcarbonyle en C2-C6 ou alcoxycarbonyle en C2-C6; et
    • n a la valeur de 0, de 1 ou de 2.
  4. Composition comprenant: au moins un composé choisi parmi le groupe constitué d'un composé de formule I tel que défini dans la revendication 1, un N-oxyde ou un sel de celui-ci, et un composé de formule II tel que défini dans la revendication 1, un N-oxyde ou un sel de celui-ci; et au moins un autre composé ou agent biologiquement actif.
  5. Composition selon la revendication 4, comprenant en outre un composant supplémentaire choisi parmi le groupe constitué d'un agent de surface, d'un diluant solide, et d'un diluant liquide.
  6. Composition selon la revendication 4, dans laquelle l'autre composé ou agent biologiquement actif est choisi parmi le groupe constitué d'un autre insecticide, d'un fongicide, d'un nématicide, d'un bactéricide, d'un acaricide, d'un régulateur de croissance, d'un stimulant racinaire, d'un chimiostérilisant, d'une substance sémiochimique, d'un répulsif, d'un attractif, d'une phéromone, d'un phagostimulant, et d'une bactérie, d'un virus ou d'un champignon entomopathogènes.
  7. Composition selon la revendication 6, dans laquelle l'autre insecticide est choisi parmi le groupe constitué d'un pyréthroïde, d'un carbamate, d'un néonicotinoïde, d'un agent bloquant du canal sodique neuronal, d'une lactone macrocyclique insecticide, d'un antagoniste de l'acide γ-aminobutyrique (GABA), d'une urée insecticide, d'un agent mimétique de l'hormone juvénile, d'une pymétrozine, et d'un amitraz.
  8. Composition selon la revendication 6, dans laquelle l'autre insecticide est choisi parmi le groupe constitué de l'abamectine, de l'acéphate, de l'acétamipride, de l'avermectine, de l'azadirachtine, de l'azinphos-méthyle, de la bifenthrine, du binfénazate, de la buprofézine, du carbofurane, du chlorfénapyr, du chlorfluazuron, du chlorpyrifos, du chlorpyrifos-méthyle, du chromafénozide, de la clothianidine, de la cyfluthrine, de la bêta-cyfluthrine, de la cyhalothrine, de la lambda-cyhalothrine, de la cyperméthrine, de la cyromazine, de la deltaméthrine, du diafenthiuron, du diazinon, du diflubenzuron, du diméthoate, du diofénolan, de l'émamectine, de l'endosulfan, de l'esfenvalérate, de l'éthiprole, du fénothicarb, du fénoxycarb, de la fenpropathrine, du fenproximate, de la fenvalérate, du fipronil, du flonicamide, du flucythrinate, du tau-fluvalinate, du flufénoxuron, du fonophos, de l'halofénozide, de l'hexaflumuron, de l'imidaclopride, de l'indoxacarb, de l'isofenphos, du lufénuron, du malathion, du métaldéhyde, du méthamidophos, du méthidathion, du méthomyl, du méthoprène, du méthoxychlor, du monocrotophos, du méthoxyfénozide, de la nithiazine, du novaluron, de l'oxamyle, du parathion, du parathion-méthyle, de la perméthrine, du phorate, de la phosalone, du phosmet, du phosphamidon, du pirimicarb, du profénofos, de la pymétrozine, du pyridalyle, du pyriproxyfène, de la roténone, du spinosad, du sulprofos, du tébufénozide, du téflubenzuron, de la téfluthrine, du terbufos, du tétrachlorvinphos, du thiaclopride, du thiaméthoxame, du thiodicarb, du thiosultap-sodium, de la tralométhrine, du trichlorfon et du triflumuron, de l'aldicarb, de l'oxamyl, du fénamiphos, de l'amitraz, du chinométhionate, du chlorobenziate, de la cyhexatine, du dicofol, du diénochlor, de l'étoxazole, du fénazaquin, de l'oxyde de fenbutatine, de la fenpropathrine, du fenpyroximate, de l'hexythiazox, du propargite, du pyridabène et le tébufenpyrad, duBacillus thuringiensis, de la delta endotoxine de Bacillus thuringiensis, et des bactéries, virus et champignons entomopathogènes.
  9. Composition selon la revendication 6, dans laquelle l'autre insecticide est choisi parmi le groupe constitué de la cyperméthrine, de la cyhalothrine, de la cyfluthrine, de la bêta-cyfluthrine, de l'esfenvalérate, du fenvalérate, de la tralométhrine, du fénothicarb, du méthomyl, de l'oxamyle, du thiodicarb, de la clothianidine, de l'imidaclopride, du thiaclopride, de l'indoxacarb, du spinosad, de l'abamectine, de l'avermectine, de l'émamectine, de l'endosulfan, de l'éthiprole, du fipronil, du flufénoxuron, du triflumuron, du diofénolan, du pyriproxyfène, de la pymétrozine, de l'amitraz, du Bacillus thuringiensis, de l'endotoxine delta de Bacillus thuringiensis et champignons entomophages.
  10. Procédé de contrôle d'au moins un animal nuisible invertébré, comprenant:
    • la mise en contact de l'animal nuisible invertébré ou de son environnement avec une quantité biologiquement efficace d'une composition selon la revendication 4 ou la revendication 5.
  11. Composé selon la formule II tel que défini dans la revendication 1, un N-oxyde de celui-ci ou un sel de celui-ci.
  12. Composé selon la revendication 11, dans lequel
    • A et B représentent tous deux O;
    • R1 représente un atome H, un groupe alkyle en C1-C4, alcényle en C2-C4, alcynyle en C2-C4, cycloalkyle en C3-C6, alkylcarbonyle en C2-C6 ou alcoxycarbonyle en C2-C6; et
    • n a la valeur de 0, de 1 ou de 2.
  13. Composé selon la revendication 12, dans lequel
    • J représente un cycle phényle ou un noyau hétéroaromatique à 5 ou 6 chaînons choisi parmi le groupe constitué de J-1, J-2, J-3 et J-4, chaque cycle J éventuellement substitué avec 1 à 3 R5
    • Q représente O, S ou NR5;
    • W, X, Y et Z représentent indépendamment N ou CR5, à condition que dans J-3 et J-4 au moins un élément parmi le groupe constitué de W, X, Y et Z représente un atome N;
    • R2 représente H, un alkyle en C1-C4, un alcényle en C2-C4, un alcynyle en C2-C4, un cycloalkyle en C3-C6, un alkylcarbonyle en C2-C6 ou un alcoxycarbonyle en C2-C6;
    • R3 représente H, un alkyle en C1-C6, un alcényle en C2-C6, un alcynyle en C2-C6 ou un cycloalkyle en C3-C6 chacun éventuellement substitué avec un ou plusieurs substituant(s) choisi(s) parmi le groupe constitué d'un halogène, CN, un alcoxy en C1-C2, un alkylthio en C1-C2, un alkylsulfinyle en C1-C2 et un alkylsulfonyle en C1-C2;
    • chaque R4 représente indépendamment un alkyle en C1-C4, un alkyle en C1-C4 halogéné, un halogène, CN, NO2, un alcoxy en C1-C4, un alcoxy en C1-C4 halogéné, un alkylthio en C1-C4, un alkylsulfinyle en C1-C4, un alkylsulfonyle en C1-C4, un alkylthio en C1-C4 halogéné, un alkylsulfinyle en C1-C4 halogéné ou un alkylsulfonyle en C1-C4 halogéné;
    • chaque R5 représente indépendamment H, un alkyle en C1-C4, un alkyle en C1-C6 halogéné, un halogène, CN, NO2, un alcoxy en C1-C4, un alcoxy en C1-C4 halogéné, un alkylthio en C1-C4, un alkylsulfinyle en C1-C4, un alkylsulfonyle en C1-C4, un alkylthio en C1-C4 halogéné, un alkylsulfinyle en C1-C4 halogéné, un alkylsulfonyle en C1-C4 halogéné ou un alcoxycarbonyle en C2-C4, un alkylaminocarbonyle en C2-C6, un dialkylaminocarbonyle en C3-C8; ou
    • chaque R5 représente indépendamment un phényle, un benzyle ou un noyau hétéroaromatique à 5 ou 6 chaînons, chaque cycle éventuellement substitué avec un alkyle en C1-C4, un alcényle en C2-C4, un alcynyle en C2-C4, un cycloalkyle en C3-C6, un alkyle en C1-C4 halogéné, un alcényle en C2-C4 halogéné, un alcynyle en C2-C4 halogéné, un cycloalkyle en C3-C6 halogéné, un halogène, CN, NO2, un alcoxy en C1-C4, un alcoxy en C1-C4 halogéné, un alkylthio en C1-C4, un alkylsulfinyle en C1-C4, un alkylsulfonyle en C1-C4, un alkylamino en C1-C4, un dialkylamino en C2-C8, un cycloalkylamino en C3-C6, un (alkyl)cycloalkylamino en C3-C6, un alkylcarbonyle en C2-C4, un alcoxycarbonyle en C2-C6, un alkylaminocarbonyle en C2-C6, un dialkylaminocarbonyle en C3-C8, ou un trialkylsilyle en C3-C6; ou
    • deux groupes R5 lorsque fixés à des atomes de carbone adjacents peuvent être pris conjointement comme -OCF2O-, -CF2CF2O- ou -OCF2CF2O-.
  14. Composé selon la revendication 13, dans lequel
    • R2 représente H;
    • R3 représente un groupe alkyle en C1-C4; et
    • au moins un R5 est autre que H et est fixé à J en position ortho par rapport à la fraction N(R1)C(=B).
  15. Composition comprenant:
    • au moins un composé selon la revendication 11; et
    • au moins un composant supplémentaire choisi parmi le groupe constitué d'un agent de surface, d'un diluant solide, d'un diluant liquide et d'un autre composé ou agent biologiquement actif.
  16. Procédé de contrôle d'au moins un animal nuisible invertébré, comprenant: la mise en contact de l'animal nuisible invertébré ou de son environnement avec une quantité biologiquement efficace d'un composé selon la revendication 11 ou avec une quantité biologiquement efficace d'une composition selon la revendication 15.
  17. Composé de la formule Id, un N-oxyde ou un sel de celui-ci,
    dans laquelle
    • chaque J représente indépendamment un cycle phényle ou un noyau hétéroaromatique à 5 ou 6 chaînons, chaque cycle éventuellement substitué avec 1 à 4 R5;
    • A et B représentent indépendamment O ou S;
    • n a la valeur de 0, de 1, de 2 ou de 3;
    • R1 représente un H, un alkylcarbonyle en C2-C6, alcoxycarbonyle en C2-C6, alkylaminocarbonyle en C2-C6 ou dialkylaminocarbonyle en C3-C8; ou
    • R1 représente un alkyle en C1-C6, un alcényle en C2-C6, un alcynyle en C2-C6 ou un cycloalkyle en C3-C6 chacun éventuellement substitué avec un ou plusieurs substituant(s) choisi(s) parmi le groupe constitué d'un halogène, CN, NO2, un hydroxy, un alcoxy en C1-C4, un alkylthio en C1-C4, un alkylsulfinyle en C1-C4, un alkylsulfonyle en C1-C4, un alcoxycarbonyle en C2-C4, un alkylamino en C1-C4, un dialkylamino en C2-C8 et un cycloalkylamino en C3-C6;
    • R2 représente H, un alkyle en C1-C6, un alcényle en C2-C6, un alcynyle en C2-C6, un cycloalkyle en C3-C6, un alcoxy en C1-C4, un alkylamino en C1-C4, un dialkylamino en C2-C8, un cycloalkylamino en C3-C6, un alcoxycarbonyle en C2-C6, ou un alkylcarbonyle en C2-C6;
    • R3 représente H; ou
    • R3 représente un alkyle en C1-C6, un alcényle en C2-C6, un alcynyle en C2-C6 ou un cycloalkyle en C3-C6 chacun éventuellement substitué avec un ou plusieurs substituant(s) choisi(s) parmi le groupe constitué d'un halogène, CN, NO2, un hydroxy, un alcoxy en C1-C4, un alkylthio en C1-C4, un alkylsulfinyle en C1-C4 et un alkylsulfonyle en C1-C4; ou
    • R2 et R3 peuvent être pris conjointement avec l'azote auquel ils sont fixés pour former un cycle contenant 2 à 6 atomes de carbone et éventuellement un atome supplémentaire d'azote, de soufre ou d'oxygène, ledit cycle peut être éventuellement substitué avec 1 à 4 substituant(s) choisi(s) parmi le groupe constitué d'un alkyle en C1-C2, un halogène, CN, NO2 et un alcoxy en C1-C2; et
    • chaque R4 et chaque R5 représentent indépendamment H, un alkyle en C1-C6, un alcényle en C2-C6, un alcynyle en C2-C6, un cycloalkyle en C3-C6, un alkyle en C1-C6 halogéné, un alcényle en C2-C6 halogéné, un alcynyle en C2-C6 halogéné, un cycloalkyle en C3-C6 halogéné, un halogène, CN, CO2H, CONH2, NO2, un hydroxy, un alcoxy en C1-C4, un alcoxy en C1-C4 halogéné, un alkylthio en C1-C4, un alkylsulfinyle en C1-C4, un alkylsulfonyle en C1-C4, un alkylthio en C1-C4 halogéné, un alkylsulfinyle en C1-C4 halogéné, un alkylsulfonyle en C1-C4 halogéné, un alkylamino en C1-C4, un dialkylamino en C2-C8, un cycloalkylamino en C3-C6, un alkylcarbonyle en C2-C6, un alcoxycarbonyle en C2-C6, un alkylaminocarbonyle en C2-C6, un dialkylaminocarbonyle en C3-C8 ou un trialkylsilyle en C3-C6; ou
    • chaque R5 représente indépendamment un phényle, un benzyle, un phénoxy ou un noyau hétéroaromatique à 5 ou 6 chaînons, chaque cycle éventuellement substitué avec un à trois substituant(s) indépendamment choisi(s) parmi le groupe constitué d'un alkyle en C1-C4, un alcényle en C2-C4, un alcynyle en C2-C4, un cycloalkyle en C3-C6, un alkyle en C1-C4 halogéné, un alcényle en C2-C4 halogéné, un alcynyle en C2-C4 halogéné, un cycloalkyle en C3-C6 halogéné, un halogène, CN, NO2, un alcoxy en C1-C4, un alcoxy en C1-C4 halogéné, un alkylthio en C1-C4, un alkylsulfinyle en C1-C4, un alkylsulfonyle en C1-C4, un alkylamino en C1-C4, un dialkylamino en C2-C8, un cycloalkylamino en C3-C6, un (alkyl)cycloalkylamino en C3-C6, un alkylcarbonyle en C2-C4, un alcoxycarbonyle en C2-C6, un alkylaminocarbonyle en C2-C6, un dialkylaminocarbonyle en C3-C8, ou un trialkylsilyle en C3-C6; ou
    • deux groupes R5, lorsque fixés à des atomes de carbone adjacents, peuvent être pris conjointement comme -OCF2O-, -CF2CF2O- ou -OCF2CF2O-;
    • M et M1 représentent chacun indépendamment CR6R7, NR8, O ou S lorsque la liaison entre M et M1 est une simple liaison; et représentent chacun indépendamment CR6 ou N lorsque la liaison entre M et M1 est une liaison aromatique;
    • chaque R6 et chaque R7 représentent indépendamment H, un groupe alkyle en C1-C4, un halogène, CN, un groupe alkyle en C1-C4 halogéné ou alcoxy en C1-C4; et
    • chaque R8 représente indépendamment H ou un groupe alkyle en C1-C4.
  18. Composé selon la revendication 17, dans lequel
    • A et B représentent tous deux O;
    • R1 représente H, un groupe alkyle en C1-C4, alcényle en C2-C4, alcynyle en C2-C4, cycloalkyle en C3-C6, alkycarbonyle en C2-C6 ou alcoxycarbonyle en C2-C6; et
    • n a la valeur de 0, de 1 ou de 2.
  19. Composé selon la revendication 18, dans lequel
    • J représente un cycle phényle ou un noyau hétéroaromatique de 5 ou 6 chaînons choisi parmi le groupe constitué de J-1, J-2, J-3 et J-4
    • Q représente O, S ou NR5;
    • W, X, Y et Z représentent indépendamment N ou CR5, à condition que dans J-3 et J-4 au moins un élément parmi le groupe constitué de W, X, Y et Z soit N;
    • R2 représente H, un alkyle en C1-C4, un alcényle en C2-C4, un alcynyle en C2-C4, un cycloalkyle en C3-C6, un alkylcarbonyle en C2-C6 ou un alcoxycarbonyle en C2-C6;
    • R3 représente H, un alkyle en C1-C6, un alcényle en C2-C6, un alcynyle en C2-C6 ou un cycloalkyle en C3-C6 chacun éventuellement substitué avec un ou plusieurs substituant(s) choisi(s) parmi le groupe constitué d'un halogène, CN, un alcoxy en C1-C2, un alkylthio en C1-C2, un alkylsulfinyle en C1-C2 et un alkylsulfonyle en C1-C2;
    • chaque R4 représente indépendamment un alkyle en C1-C4, un alkyle en C1-C4 halogéné, un halogène, CN, NO2, un alcoxy en C1-C4, un alcoxy en C1-C4 halogéné, un alkylthio en C1-C4, un alkylsulfinyle en C1-C4, un alkylsulfonyle en C1-C4, un alkylthio en C1-C4 halogéné, un alkylsulfinyle en C1-C4 halogéné ou un alkylsulfonyle en C1-C4 halogéné;
    • chaque R5 représente indépendamment H, un alkyle en C1-C4, un alkyle en C1-C6 halogéné, un halogène, CN, NO2, un alcoxy en C1-C4, un alcoxy en C1-C4 halogéné, un alkylthio en C1-C4, un alkylsulfinyle en C1-C4, un alkylsulfonyle en C1-C4, un alkylthio en C1-C4 halogéné, un alkylsulfinyle en C1-C4 halogéné, un alkylsulfonyle en C1-C4 halogéné ou un alcoxycarbonyle en C2-C4, un alkylaminocarbonyle en C2-C6, un dialkylaminocarbonyle en C3-C8; ou
    • chaque R5 représente indépendamment un phényle, un benzyle ou un noyau hétéroaromatique à 5 ou 6 chaînons, chaque cycle éventuellement substitué avec un alkyle en C1-C4, un alcényle en C2-C4, un alcynyle en C2-C4, un cycloalkyle en C3-C6, un alkyle en C1-C4 halogéné, un alcényle en C2-C4 halogéné, un alcynyle en C2-C4 halogéné, un cycloalkyle en C3-C6 halogéné, un halogène, CN, NO2, un alcoxy en C1-C4, un alcoxy en C1-C4 halogéné, un alkylthio en C1-C4, un alkylsulfinyle en C1-C4, un alkylsulfonyle en C1-C4, un alkylamino en C1-C4, un dialkylamino en C2-C8, un cycloalkylamino en C3-C6, un (alkyl)cycloalkylamino en C3-C6, un alkylcarbonyle en C2-C4, un alcoxycarbonyle en C2-C6, un alkylaminocarbonyle en C2-C6, un dialkylaminocarbonyle en C3-C8, ou un trialkylsilyle en C3-C6; ou
    • deux groupes R5 lorsque fixés à des atomes de carbone adjacents peuvent être pris conjointement comme -OCF2O-, -CF2CF2O- ou -OCF2CF2O-.
  20. Composé selon la revendication 19, dans lequel
    • R1 représente H ou un alkyle en C1-C4;
    • R2 représente H ou un alkyle en C1-C4;
    • R3 représente H, un alkyle en C1-C4 éventuellement substitué avec un halogène, CN, OCH3, ou S(O)pCH3;
    • chaque R5 représente indépendamment un atome H, un alkyle en C1-C4, un alkyle en C1-C4 halogéné, un halogène, CN, NO2, un alcoxy en C1-C4, un alcoxy en C1-C4 halogéné, un alkylthio en C1-C4, un alkylsulfinyle en C1-C4, un alkylsulfonyle en C1-C4, un alkylthio en C1-C4 halogéné, un alkylsulfinyle en C1-C4 halogéné, un alkylsulfonyle en C1-C4 halogéné, un alcoxycarbonyle en C2-C4 ou un dialkylaminocarbonyle en C3-C8; ou un phényle, un benzyle, ou un noyau hétéroaromatique à 5 ou 6 chaînons, chaque cycle éventuellement substitué avec un halogène, CN, NO2, un alkyle en C1-C4, un alcényle en C2-C4, un alcynyle en C2-C4, un cycloalkyle en C3-C6, un alkyle en C1-C4 halogéné, un alcoxy en C1-C4 ou un alcoxy en C1-C4 halogéné;
    • à condition qu'au moins un R5 soit autre que H et soit fixé à J en position ortho par rapport à la fraction N(R1)C(=B); et
    • p a la valeur de 0, de 1 ou de 2.
  21. Composé selon la revendication 20, dans lequel
    • J représente un groupe phényle substitué, un groupe pyrazole substitué, un groupe pyrrole substitué, un groupe pyridine substitué ou un groupe pyrimidine substitué.
  22. Composé selon la revendication 21, dans lequel R1 et R2 représentent chacun un atome H.
  23. Composition comprenant au moins un composé selon la revendication 17, et au moins un composant supplémentaire choisi parmi le groupe constitué d'un agent de surface, d'un diluant solide, d'un diluant liquide et d'un autre composé ou agent biologiquement actif.
  24. Procédé de contrôle d'au moins un animal nuisible invertébré, comprenant: la mise en contact de l'animal nuisible invertébré ou de son environnement avec une quantité biologiquement efficace d'un composé selon la revendication 17 ou avec une quantité biologiquement efficace d'une composition selon la revendication 23.






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