Insecticidal tricyclic derivatives
It has now been found that certain tricyclic derivatives have provided unexpected insecticidal activity. These compounds are represented by formula I: wherein R 1 through R 8 , inclusively, and X and Y are fully described. Compositions comprising an insecticidally effective amount of at least one compound of formula I, and optionally, an effective amount of at least one of a second compound, with at least one insecticidally compatible carrier are also disclosed; along with methods of controlling insects comprising applying said compositions to the locus where insects are present or are expected to be present.
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 1 through R 8 , inclusively, are independently selected from hydrogen, halogen, alkyl, cycloalkyl, alkenyl, alkynyl, trialkylsilylalkynyl, alkoxy, haloalkyl, haloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, dialkylaminosulfonyl, nitro, cyano, amino, formyl, or alkylcarbonyl;
X is selected from —CR 9 R 10 —, —CR 11 R 12 CR 13 R 14 —, —CR 15 ═CR 16 —, NR 17 —, —CR 18 R 19 NR 20 —, or C 21 ═N—;
and
Y is selected from —CR 22 R 23 —, —CR 24 R 25 CR 26 R 27 , CR 28 CR 29 —, N 30 —, —CR 31 R 32 NR 33 —, —O—, —S—, —S(O)—, —S(O) 2 —, —CR 34 R 35 O—, —CR 36 R 37 S—, or —CR 38 ═N—;
where
R 9 and R 10 are independently selected from hydrogen, alkyl, or (piperidin-4-yl)alkyl;
or
R 9 and R 10 may be taken together with
or with ═CHC 2 H 4 NR 40 R 41 ,
where
R 39 , R 40 and R 41 are independently selected from hydrogen; alkyl; hydroxylalkyl; alkoxyalkyl; alkylthioalkyl; alkoxycarbonylalkyl; haloalkoxycarbonyl; arylalkyl; aryloxyalkyl; arylcarbonylalkyl; arylcarbonyloxyalkyl, wherein aryl is optionally substituted with one or more halogen, alkoxy, haloalkyl, or aryl;
or
R 40 and R 41 may be taken together with —C 2 H 4 N(CH 3 )C 2 H 4 — to form a piperazine ring;
u is 0 or 1,
and when u is 1, an N-oxide is formed;
n is 0, and R a is hydrogen;
or
n is 1 to 8, and R a is selected from one or more of alkyl, alkoxyalkyl, alkoxycarbonyl, and aryl, wherein aryl is optionally substituted with one or more halogen, alkoxy, haloalkyl, or aryl;
R 11 is selected from hydrogen, alkyl, alkylaminoalkoxy, dialkylaminoalkoxy, N(alkyl)(alkylaminoalkyl), N(alkyl)(dialkylaminoalkyl), alkylaminoalkylalkynyl, dialkylaminoalkylalkynyl, morpholinyl, imidazolinyl, alkylpyrrolidinyloxy,
where
v is 0 or 1,
and when v is 1, A is a bridging group selected from —O—, —S—, —NH—, and —CH 2 —;
u is as described above;
R 42 through R 45 , inclusively, are independently selected from hydrogen; alkyl; alkenyl; alkynyl; hydroxylalkyl; alkoxyalkyl; alkylthioalkyl; alkylcarbonyl; alkoxycarbonylalkyl; haloalkoxycarbonyl; arylalkyl; aryloxyalkyl; arylcarbonylalkyl; arylcarbonyloxyalkyl; heteroaryl; heteroarylalkyl; heteroarylalkylamino; wherein aryl and heteroaryl are optionally substituted with one or more halogen, alkoxy, haloalkyl, or aryl;
or
R 43 and R 44 may be taken together with —C 5 H 10 — to form a piperidine ring;
m, p, and q are 0, and R b , R c and R d are hydrogen;
or
m is 1 to 8, p is 1 to 7, and q is 1 to 10, and R b , R c , and R d , respectively, are independently selected from one or more of alkyl, alkoxyalkyl, alkylamino, dialkylamino, alkoxycarbonyl, or aryl, wherein aryl is optionally substituted with one or more halogen, alkoxy, haloalkyl, or aryl;
or
R 11 and R 12 may be taken together with
where R a , n, u, and R 39 are as described above;
R 2 , when not taken together with R 11 , and R 13 , R 14 , and R 16 , are independently selected from hydrogen, hydroxy, halogen, alkyl, alkoxy, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkoxycarbonyloxy, alkylaminocarbonyl, dialkylaminocarbonyl, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, alkylaminosulfonyl, or dialkylaminosulfonyl;
R 15 is selected from
where m, u, v, A, R b and R 42 are as described above;
R 17 is hydrogen; alkyl; alkoxyalkyl; alkoxycarbonyl; dialkylaminoalkyl; alkylaminocarbonyl; dialkylaminocarbonyl; alkylsulfonyl; aryl, and arylalkyl wherein aryl is optionally substituted with one or more halogen, alkoxy, haloalkyl, or aryl;
or —C 3 H 6 NR 47 R 48
where
A, v, and u are as described above;
R 46 is selected from selected from hydrogen; alkyl; alkenyl; alkynyl; hydroxylalkyl; alkoxyalkyl; alkylthioalkyl; alkylcarbonyl; alkoxycarbonylalkyl; haloalkoxycarbonyl; arylalkyl; aryloxyalkyl; arylcarbonylalkyl; arylcarbonyloxyalkyl; heteroaryl; heteroarylalkyl; heteroarylalkylamino; wherein aryl and heteroaryl are optionally substituted with one or more halogen, alkoxy, haloalkyl, or aryl;
R 47 and R 48 are independently selected from hydrogen and alkyl;
or
R 47 and R 48 may be taken together with —C 5 H 10 — to form a piperidine ring, or with —C 2 H 4 N(CH 3 )C 2 H 1 —, or —C 2 H(C 2 H 4 OH)C 2 H 4 — to form a piperazine ring;
R 18 and R 19 are independently selected from hydrogen, alkyl, amino, alkylaminoalkyl, and dialkylaminoalkyl;
R 20 is selected from hydrogen; alkyl; alkoxyalkyl; alkoxycarbonyl; dialkylaminoalkyl; alkylaminocarbonyl; dialkylaminocarbonyl; alkylsulfonyl; aryl, and arylalkyl wherein aryl is optionally substituted with one or more halogen, alkoxy, haloalkyl, or aryl;
R 21 is selected from hydrogen, alkyl,
where
A, v, and u are as described above;
R 49 through R 52 , inclusively, are independently selected from hydrogen; alkyl; alkenyl, alkynyl, hydroxylalkyl; alkoxyalkyl; alkylthioalkyl; alkylcarbonyl, alkoxycarbonylalkyl; haloalkoxycarbonyl; arylalkyl; aryloxyalkyl; arylcarbonylalkyl; arylcarbonyloxyalkyl, heteroaryl, heteroarylalkyl, heteroarylalkylamino, wherein aryl and heteroaryl are optionally substituted with one or more halogen, alkoxy, haloalkyl, or aryl;
or
R 50 and R 51 may be taken together with —C 5 H 10 — to form a piperidine ring;
r, s, and t are 0, and R e , R f , and R g are hydrogen,
or
r is 1 to 8, s is 1 to 7, t is 1 to 10, and R e , R f , and R g , respectively, are independently selected from one or more of alkyl, alkoxyalkyl, alkylamino, dialkylamino, alkoxycarbonyl, or aryl, wherein aryl is optionally substituted with one or more halogen, alkoxy, haloalkyl, or aryl;
R 22 through R 29 , inclusively, are independently selected from hydrogen, and alkyl;
R 30 is selected from hydrogen; alkyl; alkoxyalkyl; alkoxycarbonyl; dialkylaminoalkyl; alkylaminocarbonyl; dialkylaminocarbonyl; alkylsulfonyl; aryl, and arylalkyl wherein aryl is optionally substituted with one or more halogen, alkoxy, haloalkyl, or aryl;
R 31 and R 32 are independently selected from hydrogen, and alkyl,
R 33 is selected from hydrogen; alkyl; alkoxyalkyl; alkoxycarbonyl; dialkylaminoalkyl; alkylaminocarbonyl; dialkylaminocarbonyl; alkylsulfonyl; aryl, and arylalkyl wherein aryl is optionally substituted with one or more halogen, alkoxy, haloalkyl, or aryl;
R 34 through R 38 , inclusively, are independently selected from hydrogen, and alkyl;
and,
agriculturally acceptable salts thereof.
2 . An insecticidal composition of claim 1 , wherein X is —CR 9 R 10 — and Y is selected from —O—, —S—, —CR 22 R 23 —, and —CR 34 R 35 O—;
where
R 9 and R 10 are taken together with
where
R 39 is selected from hydrogen; alkyl; hydroxylalkyl; alkoxyalkyl; alkylthioalkyl; alkoxycarbonylalkyl; haloalkoxycarbonyl; arylalkyl; aryloxyalkyl; arylcarbonylalkyl; arylcarbonyloxyalkyl, wherein aryl is optionally substituted with one or more halogen, alkoxy, haloalkyl, or aryl;
and,
R 22 , R 1 , R 34 and R 35 are independently selected from hydrogen and alkyl.
3 . An insecticidal composition of claim 1 , wherein X is —CR 11 R 12 CR 13 R 14 — and Y is selected from —O—, —S— and —CR 22 R 23 —;
where
R 11 is selected from
where
R 42 and R 45 are independently selected from hydrogen; alkyl; alkenyl; alkynyl; hydroxylalkyl; alkoxyalkyl; alkylthioalkyl; alkylcarbonyl; alkoxycarbonylalkyl; haloalkoxycarbonyl; arylalkyl; aryloxyalkyl; arylcarbonylalkyl; arylcarbonyloxyalkyl; heteroaryl; heteroarylalkyl; heteroarylalkylamino; wherein aryl and heteroaryl are optionally substituted with one or more halogen, alkoxy, haloalkyl, or aryl;
R 12 is selected from selected from hydrogen, hydroxy, halogen, alkyl, alkoxy, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkoxycarbonyloxy, alkylaminocarbonyl, dialkylaminocarbonyl, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, alkylaminosulfonyl, and dialkylaminosulfonyl;
R 13 and R 14 are hydrogen;
and,
R 22 and R 23 are independently selected from hydrogen and alkyl.
4 . An insecticidal composition of claim 1 , wherein X is —CR 18 R 19 NR 20 — and Y is selected from —O—, —S— and —CR 22 R 23 —;
where
R 20 is selected from hydrogen, alkyl, alkoxyalkyl, alkoxycarbonyl, dialkylaminoalkyl, alkylaminocarbonyl, and dialkylaminocarbonyl; and,
R 22 and R 23 are independently selected from hydrogen and alkyl.
5 . An insecticidal composition of claim 1 , wherein X is —CR 21 ═N— and Y is selected from —S— and —CR 22 R 23 —;
where R 21 is
where
R 49 is selected from hydrogen; alkyl; alkenyl, alkynyl, hydroxylalkyl; alkoxyalkyl; alkylthioalkyl; alkylcarbonyl, alkoxycarbonylalkyl; haloalkoxycarbonyl; arylalkyl; aryloxyalkyl; arylcarbonylalkyl; arylcarbonyloxyalkyl, heteroaryl, heteroarylalkyl, heteroarylalkylamino, wherein aryl and heteroaryl are optionally substituted with one or more halogen, alkoxy, haloalkyl, or aryl;
and,
R 22 and R 23 are independently selected from hydrogen and alkyl.
6 . The insecticidal composition of claim 1 , further comprising one or more second compounds.
7 . The insecticidal composition of claim 2 , further comprising one or more second compounds.
8 . The insecticidal composition of claim 3 , further comprising one or more second compounds.
9 . The insecticidal composition of claim 4 , further comprising one or more second compounds.
10 . The insecticidal composition of claim 5 , further comprising one or more second compounds.
11 . A method of controlling insects, comprising applying an insecticidally effective amount of a composition of claim 1 to a locus where insects are present or are expected to be present.
12 . A method of controlling insects, comprising applying an insecticidally effective amount of a composition of claim 2 to a locus where insects are present or are expected to be present.
13 . A method of controlling insects, comprising applying an insecticidally effective amount of a composition of claim 3 to a locus where insects are present or are expected to be present.
14 . A method of controlling insects, comprising applying an insecticidally effective amount of a composition of claim 4 to a locus where insects are present or are expected to be present.
15 . A method of controlling insects, comprising applying an insecticidally effective amount of a composition of claim 5 to a locus where insects are present or are expected to be present.
16 . A method of controlling insects, comprising applying an insecticidally effective amount of a composition of claim 6 to a locus where insects are present or are expected to be present.
17 . A method of controlling insects, comprising applying an insecticidally effective amount of a composition of claim 7 to a locus where insects are present or are expected to be present.
18 . A method of controlling insects, comprising applying an insecticidally effective amount of a composition of claim 8 to a locus where insects are present or are expected to be present.
19 . A method of controlling insects, comprising applying all insecticidally effective amount of a composition of claim 9 to a locus where insects are present or are expected to be present.
20 . A method of controlling insects, comprising applying an insecticidally effective amount of a composition of claim 10 to a locus where insects are present or are expected to be present.