USH1996HExpiredUtility
Insecticidal photostable acid salt derivatives of N-benzyl-4-benzhydrolpiperidines
Est. expiryNov 20, 2017(expired)· nominal 20-yr term from priority
C07D 401/10A01N 43/713C07D 211/22A01N 43/40C07D 211/94A01N 47/20
28
PatentIndex Score
0
Cited by
6
References
18
Claims
Abstract
It has now been found that certain novel photostable agriculturally acceptable organic or inorganic salts of formula I are useful as insecticides:whereR is alkoxycarbonyl, alkoxycarbonylamino, cycloalkylalkoxy, 2-alkyl-2H-tetrazol-5-yl, or 2-haloalkyl-2H-tetrazol-5-yl; R1 is trihaloalkyl, or trihaloalkoxy; n is 0, or 1; and, wherein said salts are derived from hydrochloric acid; hydrobromic acid; boric acid; phosphoric acid; maleic acid; fumaric acid; phthalic acid; salicylic acid optionally substituted with alkyl or halogen; D-glucuronic acid; the sulfonic acid R2SO3H where R2 is alkyl, haloalkyl, hydroxyalkyl, D-10-camphoryl, or phenyl optionally substituted with alkyl or halogen; the carboxylic acid R3CO2H where R3 is hydrogen, alkyl, trihaloalkyl, carboxyl, phenyl optionally substituted with alkyl or halogen, or pyridyl; the boronic acid R4B(OH)2 where R4 is alkyl or phenyl optionally substituted with alkyl or halogen; the phosphonic acid R5PO3H2 where R5 is alkyl, haloalkenyl, or phenyl optionally substituted with alkyl or halogen; the sulfuric acid R6OSO3H where R6 is hydrogen or alkyl; or the alkanoic acid X-(CH2)qCO2H where q is 0 to 11, X is halogen, trihaloalkyl, haloalkenyl, cyano, aminocarbonyl, or CO2R7 where R7 is hydrogen or alkyl. Preferred compounds include those where R is 2-ethyl-2H-tetrazol-5-yl; R1 is trifluoromethyl; n is 1; and said salts are derived from hydrochloric acid, or the sulfonic acid R2SO3H where R2 is alkyl, or hydroxyalkyl.
Claims
exact text as granted — not AI-modifiedWe claim:
1. An insecticidal, photostable, agriculturally acceptable acid salt of an organic or inorganic acid having the formula:
where
R is alkoxycarbonyl, alkoxycarbonylamino, cycloalkylalkoxy, 2-alkyl-2H-tetrazol-5-yl, or 2-haloalkyl-2H-tetrazol-5-yl;
R 1 is trihaloalkyl, or trihaloalkoxy;
n is 0,or 1; and,
wherein said salt is at least about 2.5 times more photostable than its non-ionic parent and is derived from hydrochloric acid, hydrobromic acid, boric acid, phosphoric acid, maleic acid, fumaric acid, phthalic acid, D-glucuronic acid; the sulfonic acid R 2 SO 3 H where R 2 is alkyl, haloalkyl, hydroxyalkyl, D-10-camphoryl, or phenyl optionally substituted with alkyl or halogen; the carboxylic acid R 3 CO 2 H where R 3 is hydrogen, alkyl, trihaloalkyl, carboxyl, phenyl optionally substituted with alkyl or halogen, or pyridyl; the boronic acid R 4 B(OH) 2 where R 4 is alkyl or phenyl optionally substituted with alkyl or halogen; the phosphonic acid R 5 PO 3 H 2 where R 5 is alkyl, haloalkenyl, or phenyl optionally substituted with alkyl or halogen: the sulfuric acid R 6 OSO 3 H where R 6 is hydrogen or alkyl; or the alkanoic acid X-(CH 2 ) q CO 2 H where q is 0 to 11, X is halogen, trihaloalkyl, haloalkenyl, cyano, aminocarbonyl, or CO 2 R 7 where R 7 is hydrogen or alkyl; and
wherein further, the following terms whether used alone or as part of a larger moiety refer to the associated number of carbon atoms: (1) “alkyl” or “alkoxy” refers to 1 to 6 carbon atoms, (2) “alkenyl” refers to 2 to 12 carbon atoms; and (3) “cycloalkyl” refers to 3 to 8 carbon atoms.
2. The acid salt of claim 1 where R is alkoxycarbonyl, alkoxycarbonylamino, cycloalkylalkoxy, 2-alkyl-2H-tetrazol-5-yl, or 2-haloalkyl-2H-tetrazol-5-yl;
R 1 is trihaloalkyl, or trihaloalkoxy;
n is 0, or 1; and,
wherein said salt is derived from D-glucuronic acid, or the sulfonic acid R 2 SO 3 H where R 2 is alkyl, haloalkyl, hydroxyalkyl, D-10-camphoryl, or phenyl optionally substituted with alkyl or halogen.
3. The acid salt of claim 1 where R is 2-ethyl-2H-tetrazol-5-yl; R 1 is trifluoromethyl; n is 1; and said salt is derived from the sulfonic acid R 2 SO 3 H where R 2 is alkyl, or hydroxyalkyl.
4. An insecticidal composition comprising an insecticidally effective amount of an acid salt of claim 1 , and an insecticidally compatible carrier.
5. An insecticidal composition comprising an insecticidally effective amount of an acid salt of claim 2 , and an insecticidally compatible carrier.
6. An insecticidal composition comprising an insecticidally effective amount of an acid salt of claim 3 , and an insecticidally compatible carrier.
7. A method of controlling insects, comprising application of an insecticidally effective amount of a composition of claim 4 to a locus where insect control is desired.
8. A method of controlling insects, comprising application of an insecticidally effective amount of a composition of claim 5 to a locus where insect control is desired.
9. A method of controlling insects, comprising application of an insecticidally effective amount of a composition of claim 6 to a locus where insect control is desired.
10. An insecticidal, photostable, agriculturally acceptable salt of an organic or inorganic acid having the formula:
wherein the acid employed to form said salt, and n, q, X, R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 are as set forth in the following table:
Photostable N-Benzyl-4-benzhydrol-
piperidine Salt Derived From The Sulfonic
Acid R 2 SO 3 H or Other Acid, Wherein:
Cmpd. No. is
R is
R 1 is
n is
R 2 is
Other Acid is
1
CO 2 CH(CH 3 ) 2
OCF 3
0
—
HCl
2
CO 2 CH(CH 3 ) 2
OCF 3
0
C 2 H 5
—
3
2-methyl-2H-tetrazol-5-yl
CF 3
0
—
HCl
4
2-methyl-2H-tetrazol-5-yl
OCF 3
0
—
HCl
5
2-methyl-2H-tetrazol-5-yl
OCF 3
0
C 2 H 5
—
6
2-ethyl-2H-tetrazol-5-yl
CF 3
0
—
HCl
7
2-ethyl-2H-tetrazol-5-yl
CF 3
0
C 2 H 5
—
8
2-ethyl-2H-tetrazol-5-yl
OCF 3
0
—
HCl
9
2-ethyl-2H-tetrazol-5-yl
OCF 3
0
C 2 H 5
—
10
2-(2-fluoroethyl-2H-tetrazol-5-yl
OCF 3
0
—
HCl
11
Cyclopropylmethoxy
CF 3
1
—
HCl
12
Cyclopropylmethoxy
CF 3
1
C 2 H 5
—
13
Cyclopropylmethoxy
CF 3
1
C 2 H 4 OH
—
15
Cyclopropylmethoxy
CF 3
1
—
D-glucuronic acid
16
NHCO 2 CH 3
OCF 3
1
—
HCl
17
NHCO 2 CH 3
OCF 3
1
C 2 H 5
—
18
NHCO 2 CH 3
OCF 3
1
C 2 H 4 OH
—
20
NHCO 2 CH 3
OCF 3
1
—
D-glucuronic acid
21
NHCO 2 CH(CH 3 ) 2
CF 3
1
—
HCl
22
NHCO 2 CH(CH 3 ) 2
CF 3
1
C 2 H 5
—
23
NHCO 2 CH(CH 3 ) 2
CF 3
1
C 2 H 4 OH
—
25
NHCO 2 CH(CH 3 ) 2
CF 3
1
—
D-glucuronic acid
26
2-methyl-2H-tetrazol-5-yl
CF 3
0
—
HCl
27
2-methyl-2H-tetrazol-5-yl
CF 3
0
C 2 H 5
—
28
2-methyl-2H-tetrazol-5-yl
CF 3
0
C 2 H 4 OH
—
30
2-methyl-2H-tetrazol-5-yl
CF 3
1
—
D-glucuronic acid
31
2-ethyl-2H-tetrazol-5-yl
CF 3
1
—
HCl
32
2-ethyl-2H-tetrazol-5-yl
CF 3
1
CH 3
—
33
2-ethyl-2H-tetrazol-5-yl
CF 3
1
C 2 H 5
—
34
2-ethyl-2H-tetrazol-5-yl
CF 3
1
C 5 H 11
—
35
2-ethyl-2H-tetrazol-5-yl
CF 3
1
C 6 H 11
—
36
2-ethyl-2H-tetrazol-5-yl
CF 3
1
CF 3
—
37
2-ethyl-2H-tetrazol-5-yl
CF 3
1
C 6 H 5
—
38
2-ethyl-2H-tetrazol-5-yl
CF 3
1
4-(CH 3 )C 6 H 4
—
39
2-ethyl-2H-tetrazol-5-yl
CF 3
1
2,4,6-(CH 3 ) 3 C 6 H 2
—
40
2-ethyl-2H-tetrazol-5-yl
CF 3
1
D-10-camphor
—
41
2-ethyl-2H-tetrazol-5-yl
CF 3
1
C 2 H 4 OH
—
44
2-ethyl-2H-tetrazol-5-yl
CF 3
1
—
D-glucuronic acid
45
2-ethyl-2H-tetrazol-5-yl
CF 3
0
CH 3
—
46
2-ethyl-2H-tetrazol-5-yl
CF 3
0
—
HBr
47
2-ethyl-2H-tetrazol-5-yl
CF 3
0
4-(CH 3 )C 6 H 4
—
48
2-ethyl-2H-tetrazol-5-yl
CF 3
0
—
D-glucuronic acid
49
2-ethyl-2H-tetrazol-5-yl
CF 3
0
C 2 H 4 OH
—
52
2-ethyl-2H-tetrazol-5-yl
CF 3
1
4-ClC 6 H 4
—
53
2-ethyl-2H-tetrazol-5-yl
CF 3
1
—
H 3 BO 3
54
2-ethyl-2H-tetrazol-5-yl
CF 3
1
—
H 3 PO 4
55
2-ethyl-2H-tetrazol-5-yl
CF 3
1
—
maleic acid
56
2-ethyl-2H-tetrazol-5-yl
CF 3
1
—
fumaric acid
57
2-ethyl-2H-tetrazol-5-yl
CF 3
1
—
phthalic acid
Photostable N-Benzyl-4-benzhydrol-
piperidine Salt Derived From The
Carboxilic Acid R 3 CO 2 H, Wherein:
Cmpd. No. is
R is
R 1 is
n is
R 3 is
58
2-ethyl-2H-tetrazol-5-yl
CF 3
1
H
59
2-ethyl-2H-tetrazol-5-yl
CF 3
1
CH 3
60
2-ethyl-2H-tetrazol-5-yl
CF 3
1
CF 3
61
2-ethyl-2H-tetrazol-5-yl
CF 3
1
CO2H
62
2-ethyl-2H-tetrazol-5-yl
CF 3
1
4-Cl-phenyl
63
2-ethyl-2H-tetrazol-5-yl
CF 3
1
4-CH 3 -phenyl
64
2-ethyl-2H-tetrazol-5-yl
CF 3
1
pyridin-2-yl
65
2-ethyl-2H-tetrazol-5-yl
CF 3
1
CH 3
66
2-ethyl-2H-tetrazol-5-yl
CF 3
1
4-Cl-phenyl
67
2-ethyl-2H-tetrazol-5-yl
CF 3
1
4-CH 3 -phenyl
Photostable N-Benzyl-4-benzhydrol-
piperidine Salt Derived From The
Phosphonic Acid R 5 PO 3 H 2 , Wherein:
Cmpd. No. is
R is
R 1 is
n is
R 5 is
68
2-ethyl-2H-tetrazol-5-yl
CF 3
1
CH 3
69
2-ethyl-2H-tetrazol-5-yl
CF 3
1
4-Cl-phenyl
70
2-ethyl-2H-tetrazol-5-yl
CF 3
1
4-CH 3 -phenyl
71
2-ethyl-2H-tetrazol-5-yl
CF 3
1
CH 2 CF═CF 2
Photostable N-Benzyl-4-benzhydrol-
piperidine Salt Derived From The
Sulfuric Acid R 6 OSO 3 H, Wherein:
Cmpd. No. is
R is
R 1 is
n is
R 6 is
72
2-ethyl-2H-tetrazol-5-yl
CF 3
1
H
73
2-ethyl-2H-tetrazol-5-yl
CF 3
1
CH 3
Photostable N-Benzyl-4-benzhydrol-
piperidine Salt Derived From The Alkanoic
Acid X—(CH 2 ) q CO 2 H, Wherein:
Cmpd. No. is
R is
R 1 is
n is
q is
X is
R 7 is
74
2-ethyl-2H-tetrazol-5-yl
CF 3
1
2
Cl
—
75
2-ethyl-2H-tetrazol-5-yl
CF 3
1
2
CF 3
—
76
2-ethyl-2H-tetrazol-5-yl
CF 3
1
1
CF═CF 2
—
77
2-ethyl-2H-tetrazol-5-yl
CF 3
1
1
CN
—
78
2-ethyl-2H-tetrazol-5-yl
CF 3
1
2
CONH 2
—
79
2-ethyl-2H-tetrazol-5-yl
CF 3
1
4
CO 2 R 7
H
80
2-ethyl-2H-tetrazol-5-yl
CF 3
1
8
CO 2 R 7
CH 3 ;
and wherein said salt is at least about 2.5 times more photostable than its non-ionic parent.
11. An insecticidal composition comprising an insecticidally effective amount of an acid salt of claim 10 , and an insecticidally compatible carrier.
12. A method of controlling insects, comprising application of an insecticidally effective amount of a composition of claim 10 to a locus where insect control is desired.
13. A method for enhancing the photostability of a N-benzyl-4-benzhydrolpiperidine or its corresponding N-oxide, comprising forming said piperidine or N-oxide as an agriculturally acceptable organic or inorganic acid salt, with the proviso that salts formed with salicylic acid, 5-chlorosalicylic acid, or 3,5-dichlorosalicylic acid are excluded.
14. The method of claim 13 , wherein said piperidine or N-oxide thereof have the formula
where R is alkoxycarbonyl, alkoxycarbonylamino, cycloalkylalkoxy, 2-alkyl-2H-tetrazol-5-yl, or 2-haloalkyl-2H-tetrazol-5-yl; R 1 is trihaloalkyl, or trihaloalkoxy; and n is 0, or 1.
15. The method of claim 14 , wherein R is 2-ethyl-2H-tetrazol-5-yl; R 1 is trifluoromethyl; and n is 1.
16. The method of claim 13 , wherein said salt is derived from hydrochloric acid, hydrobromic acid, boric acid, phosphoric acid, maleic acid, fumaric acid, phthalic acid, D-glucuronic acid; the sulfonic acid R 2 SO 3 H where R 2 is alkyl, haloalkyl, hydroxyalkyl, D-10-camphoryl, or phenyl optionally substituted with alkyl or halogen; the carboxylic acid R 3 CO 2 H where R 3 is hydrogen, alkyl, trihaloalkyl, carboxyl, phenyl optionally substituted with alkyl or halogen, or pyridyl; the boronic acid R 4 B(OH) 2 where R 4 is alkyl or phenyl optionally substituted with alkyl or halogen; the phosphonic acid R 5 PO 3 H 2 where R 5 is alkyl, haloalkenyl, or phenyl optionally substituted with alkyl or halogen: the sulfuric acid R 6 OSO 3 H where R 6 is hydrogen or alkyl; or the alkanoic acid X-(CH 2 ) q CO 2 H where q is 0 to 11, X is halogen, trihaloalkyl, haloalkenyl, cyano, amino-carbonyl, or CO 2 R 7 where R 7 is hydrogen or alkyl.
17. The method of claim 16 , wherein said salt is derived from hydrochloric acid, D-glucuronic acid, or the sulfonic acid wherein R 2 is alkyl, haloalkyl, hydroxyalkyl, D-10-camphoryl, or phenyl optionally substituted with alkyl or halogen.
18. The method of claim 13 , wherein R is 2-ethyl-2H-tetrazol-5-yl; R 1 is trifluoromethyl; n is 1; and said salts are derived from hydrochloric acid, D-glucuronic acid, or the sulfonic acid wherein R 2 is alkyl or hydroxyalkyl.Cited by (0)
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