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US 5,633,271 AGranted
Arthropodicidal oxazolines and thiazolines
AssigneeE. I. Du Pont de Nemours and Company
InventorsVictor E. Amoo, George P. Lahm, Thomas M. Stevenson
Life of this patent
Estimating the term…
Abstract
Arthropodicidally active compounds, compositions and a method for using them, the compounds having the formula ##STR1## wherein A, Q, Z, (E).sub.q, R.sup.1 and R.sup.2 are as defined in the text.
Claims11
A compound of the formula ##STR51## wherein:
- A is selected from the group a direct bond and C.sub.1 -C.sub.3 straight or branched chain alkylene;
- E is selected from the group C.sub.1 -C.sub.4 alkyl and C.sub.1 -C.sub.4 haloalkyl;
- Z is selected from the group O and S;
- q is 0, 1, 2 or 3;
- Q is a 5- to 16- membered aromatic ring system selected from the group:
- (i) monocylic aromatic ring containing 1 to 4 heteroatoms independently selected from the group 0-4 nitrogen, 0-1 oxygen, and 0-1 sulfur;
- (ii) fused carbobicyclic ring containing 8 to 12 carbons, with the proviso that when the ring is naphthyl and is on the oxazoline ring carbon adjacent to the oxazoline ring oxygen, and when E is CH.sub.3 and q is 1, then R.sup.1 is other than H;
- (iii) fused carbotricyclic ring containing 12 to 16 carbons;
- (iv) fused bicylic ring containing 1 to 4 heteroatoms independently selected from the group 0-4 nitrogen, 0-2 oxygen, and 0-2 sulfur;
- (v) fused tricylic ring containing 1 to 6 heteroatoms independently selected from the group 0-4 nitrogen, 0-2 oxygen, and 0-2 sulfur;
- and
- (vi) phenyl substituted with M-J.sup.1 ;
- Q being substituted with 1 to 6 substituents selected independently from the group R.sup.3, R.sup.4, (R.sup.5) and (R.sup.6).sub.m ;
- R.sup.1 and R.sup.2 are independently selected from the group H, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 haloalkoxy, C.sub.1 -C.sub.6 alkylthio, CN and NO.sub.2 ;
- R.sup.3 and R.sup.5 are independently selected from the group H, halogen, C.sub.1 -C.sub.16 alkyl, C.sub.1 -C.sub.16 haloalkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.16 cycloalkylalkyl, C.sub.2 -C.sub.16 alkenyl, C.sub.2 -C.sub.16 haloalkenyl, C.sub.2 -C.sub.16 alkynyl, C.sub.2 -C.sub.16 haloalkynyl, C.sub.2 -C.sub.16 alkoxyalkoxy, OR.sup.7, R.sup.7 OC(O)--, R.sup.7 C(O)--, Si(R.sup.13)(R.sup.14)R.sup.15 and M-J;
- R.sup.4 is selected from the group H, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 haloalkyl and C.sub.1 -C.sub.6 haloalkoxy;
- R.sup.6 is selected from the group H, halogen, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 haloalkoxy;
- and phenyl optionally substituted with R.sup.8 ;
- R.sup.7 is selected from the group C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl, C.sub.1 -C.sub.16 alkyl, C.sub.1 -C.sub.16 haloalkyl, C.sub.2 -C.sub.16 alkenyl, C.sub.2 -C.sub.16 haloalkenyl, C.sub.2 -C.sub.16 alkynyl and C.sub.2 -C.sub.16 haloalkynyl;
- R.sup.8 is selected from the group halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 haloalkoxy and Si(R.sup.9)(R.sup.10)R.sup.11 ;
- R.sup.9, R.sup.10 and R.sup.11 are independently C.sub.1 -C.sub.12 alkyl;
- M is selected from the group a direct bond, S, O, C(.dbd.O), C(=O)O--C.sub.1 -C.sub.2 alkylene, C.sub.1 -C.sub.4 alkylene, O--C.sub.1 -C.sub.4 alkylene and O--C.sub.2 -C.sub.4 alkenylene, wherein when M is O--C.sub.1 -C.sub.4 alkylene or O--C.sub.2 -C.sub.4 alkenylene, the oxygen atom is attached to either ring and when M is C(.dbd.O)O--C.sub.1 -C.sub.2, the C(.dbd.O) is attached to either ring;
- J is selected from the group phenyl optionally substituted with independently selected substituents (R.sup.12).sub.n ;
- and a 5-or 6-membered aromatic ring, attached through carbon or nitrogen, containing 1 to 4 heteroatoms independently selected from the group 0-4 nitrogen, 0-1 oxygen, and 0-1 sulfur, the ring optionally substituted with independently selected substituents (R.sup.12).sub.n ;
- J.sup.1 is selected from the group a 5- membered aromatic ring, attached through carbon or nitrogen, containing 1 to 4 heteroatoms independently selected from the group 0-4 nitrogen, 0-1 oxygen, and 0-1 sulfur, and a 6-membered ring containing 2 to 4 nitrogen atoms each ring optionally substituted with independently selected substituents (R.sup.12).sub.n ;
- R.sup.12 is selected from the group halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 haloalkoxy and Si(R.sup.13)(R.sup.14)R.sup.15 ;
- R.sup.13, R.sup.14 and R.sup.15 are independently C.sub.1 -C.sub.12 alkyl;
- m and n are integers independently selected from 1 to 4;
- and
- p is 1 or 2.
27 more elements
A method for controlling arthropods comprising applying to the arthropods or their environment an arthropodicidally effective amount of a compound of the formula ##STR55## wherein:
- A is selected from the group a direct bond and C.sub.1 -C.sub.3 straight or branched chain alkylene;
- E is selected from the group C.sub.1 -C.sub.4 alkyl and C.sub.1 -C.sub.4 haloalkyl;
- Z is selected from the group O and S;
- q is 0, 1, 2 or 3;
- Q is a 5- to 16- membered aromatic ring system selected from the group:
- (i) monocylic aromatic ring containing 1 to 4 heteroatoms independently selected from the group 0-4 nitrogen, 0-1 oxygen, and 0-1 sulfur;
- (ii) fused carbobicyclic ring containing 8 to 12 carbons;
- (iii) fused carbotricyclic ring containing 12 to 16 carbons;
- (iv) fused bicylic ring containing 1 to 4 heteroatoms independently selected from the group 0-4 nitrogen, 0-2 oxygen, and 0-2 sulfur;
- (v) fused tricylic ring containing 1 to 6 heteroatoms independently selected from the group 0-4 nitrogen, 0-2 oxygen, and 0-2 sulfur;
- and
- (vi) phenyl substituted with M-J.sup.1 ;
- Q being substituted with 1 to 6 substituents selected independently from the group R.sup.3, R.sup.4, (R.sup.5).sub.p and (R.sup.6).sub.m ;
- R.sup.1 and R.sup.2 are independently selected from the group H, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 haloalkoxy, C.sub.1 -C.sub.6 alkylthio, CN and NO.sub.2 ;
- R.sup.3 and R.sup.5 are independently selected from the group H, halogen, C.sub.1 -C.sub.16 alkyl, C.sub.1 -C.sub.16 haloalkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.16 cycloalkylalkyl, C.sub.2 -C.sub.16 alkenyl, C.sub.2 -C.sub.16 haloalkenyl, C.sub.2 -C.sub.16 alkynyl, C.sub.2 -C.sub.16 haloalkynyl, C.sub.2 -C.sub.16 alkoxyalkoxy, OR.sup.7, R.sup.7 OC(O)--, R.sup.7 C(O)--, Si(R.sup.13)(R.sup.14)R.sup.15 and M-J;
- R.sup.4 is selected from the group H, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 haloalkyl and C.sub.1 -C.sub.6 haloalkoxy;
- R.sup.6 is selected from the group H, halogen, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 haloalkoxy;
- and phenyl optionally substituted with R.sup.8 ;
- R.sup.7 is selected from the group C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl, C.sub.1 -C.sub.16 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.16 alkenyl;
- C.sub.2 -C.sub.16 haloalkenyl, C.sub.2 -C.sub.16 alkynyl and C.sub.2 -C.sub.16 haloalkynyl;
- R.sup.8 is selected from the group halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 haloalkoxy and Si(R.sup.9)(R.sup.10)R.sup.11 ;
- R.sup.9, R.sup.10 and R.sup.11 are independently C.sub.1 -C.sub.12 alkyl;
- M is selected from the group a direct bond, S, O, C(.dbd.O), C(.dbd.O)O--C.sub.1 -C.sub.2 alkylene, C.sub.1 -C.sub.4 alkylene, O--C.sub.1 -C.sub.4 alkylene and O--C.sub.2 -C.sub.4 alkenylene, wherein when M is O--C.sub.1 -C.sub.4 alkylene or O--C.sub.2 -C.sub.4 alkenylene, the oxygen atom is attached to either ring and when M is C(.dbd.O)O--C.sub.1 -C.sub.2, the C(.dbd.O) is attached to either ring;
- J is selected from the group phenyl optionally substituted with independently selected substituents (R.sup.12).sub.n ;
- and a 5-or 6-membered aromatic ring, attached through carbon or nitrogen, containing 1 to 4 heteroatoms independently selected from the group 0-4 nitrogen, 0-1 oxygen, and 0-1 sulfur, the ring optionally substituted with independently selected substituents (R.sup.12).sub.n ;
- J.sup.1 is selected from the group a 5-membered aromatic ring, attached through carbon or nitrogen, containing 1 to 4 heteroatoms independently selected from the group 0-4 nitrogen, 0-1 oxygen, and 0-1 sulfur, and a 6-membered ring containing 2 to 4 nitrogen atoms each ring optionally substituted with independently selected substituents (R.sup.12).sub.n ;
- R.sup.12 is selected from the group halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 haloalkoxy and Si(R.sup.13)(R.sup.14)R.sup.15 ;
- R.sup.13, R.sup.14 and R.sup.15 are independently C.sub.1 -C.sub.12 alkyl;
- m and n are integers independently selected from 1 to 4;
- and
- p is 1 or 2.
28 more elements
Dependencies are inferred from the claim text.