Pesticidal heterocycles

1. An insecticidal composition comprising at least one of an insecticidally effective amount of a compound of formula I and at least one insecticidally compatible carrier therefor, wherein the compound of formula I is:

wherein

—R and R 1 are independently selected from hydrogen and alkyl;

—R 2 and R 3 are taken together to form a five- or six-membered ring selected from ═NC(R 6 )═C(R 7 )N(R 8 )—, ═CHC(R 6 )═C(R 7 )N(R 8 )—, ═CHN═C(R 7 )N(R 8 )—, ═N(CH 2 ) 3 N(R 8 )—, ═NCH(R 6 )CH(R 7 )S—, ═NCH(R 6 )CH(R 7 )O—, ═CHCH═CHCH═N—, ═NN═CHN(R 8 )—, ═NN═NN(R 8 )—, —OCH(R 6 )CH(R 7 )N(R 8 )N═, and tautomers thereof;

where

R 6 and R 7 are independently selected from hydrogen and alkyl;

R 8 is selected from hydrogen, alkyl, amino, nitro, cyano, formyl, —CH 2 R 9 —, —CH 2 OR 9 , —C(O)R 9 ,—C(O)OR 9 , —CH 2 OC(O)R 9 ,—C(O)N(R 9 )(R 10 ), —S(O) n R 9 —, —S(O) n N(R 9 )(R 10 ) where n is 0, 1, or 2, —Si(R 9 ) 3 , —CH═N(R 9 ), —P(O)(OR 9 )(OR 10 ), —P(O)(NR 9 R 10 )(NR 9 R 10 ), and Y, wherein Y represents i) an N-oxide of said five- or six-membered ring, or ii) forms an OR a linkage wherein R a is selected from hydrogen and alkyl; and,

R 9 and R 10 are independently selected from hydrogen, alkyl, alkylcarbonyl, alkoxycarbonyl aryl, arylalkyl, and heteroaryl, wherein aryl is optionally substituted with one or more substituent independently selected from halogen, alkyl, or haloalkyl;

—R 4 and R 5 taken together are —C(R 11 )═C(R 12 )C(R 13 )═C(R 14 )—,

where

R 11 and R 14 are independently selected from hydrogen, halogen, and methyl;

R 12 is selected from hydrogen, halogen, amino, (C 1 -C 2 )alkyl, methoxy, halomethoxy, (C 2 -C 3 )alkenyl, and (C 2 -C 3 )alkynyl; and

R 13 is selected from hydrogen, halogen, cyano, (C 1 -C 2 )alkyl, hydroxyl, methoxy, halomethyl, and (C 2 -C 3 )alkynyl;

—X is selected from —O—, —OCH 2 —, —S—, and —SCH 2 —; and

agriculturally-acceptable salts thereof.

2. An insecticidal composition of claim 1 , wherein R 2 and R 3 taken together is ═NC(R 6 )═C(R 7 )N(R 8 )—, or ═CHN═C(R 7 )N(R 8 )—, and tautomers thereof, where R 8 is selected from hydrogen, cyano, —S(O) n N(R 9 )(R 10 ), and —P(O)(OR 9 )(OR 10 ), where n is 2, and R 9 and R 10 are independently selected from hydrogen and alkyl; R 4 and R 5 are taken together to form a fused ring, where R 4 and R 5 together is —C(R 11 )═C(R 12 )C(R 13 )═C(R 14 ), where R 11 is hydrogen, R 12 is selected from halogen and methoxy, and R 13 is selected from halogen and (C 1 -C 2 )alkyl; and, X is selected , —OCH 2 —, and —SCH 2 —.

3. An insecticidal composition of claim 2 , wherein R 9 and R 10 are each methyl; R 12 is selected from chlorine and methoxy; R 13 is selected from chlorine and methyl; and, R 14 is selected from hydrogen, chlorine and methyl; and X is OCH 2 —.

4. An insecticidal composition of claim 3 , wherein R 2 and R 3 taken together is ═NC(R 6 )═C(R 7 )N(R 8 )—.

5. An insecticidal composition of claim 3 , wherein R 2 and R 3 taken together is ═CHN═C(R 7 )N(R 8 )—.

6. An insecticidal composition of claim 1 , further comprising one or more second compounds.

7. An insecticidal composition of claim 2 , further comprising one or more second compounds.

8. An insecticidal composition of claim 3 , further comprising one or more second compounds.

9. An insecticidal composition of claim 4 , further comprising one or more second compounds.

10. An insecticidal composition of claim 5 , further comprising one or more second compounds.