US4412856A
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Herbicidal heterocyclic and substituted phenyl phenylacetylene amines
Assignee: Novartis Corp
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Filing: 1981-05-22
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Granted: 1983-11-01
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Expires: 2001-05-22
Abstract
Abstract The novel compounds of the formula I are useful selective herbicides for postemergence application in crops of cereals, maize and rice. In formula I, <IMAGE> (I) A is an unsubstituted or substituted amino group, Q is a C2-C6alkylene bridge, Y is an oxygen or sulfur atom or an unsubstituted or substituted nitrogen atom, and Z is an unsubstituted or substituted phenyl, naphthyl or heterocyclic radical, which phenyl radical, containing the bridge member Y, can additionally carry one to four further substituents.
Inventors
- 👤 Hans-Georg Brunner
- 👤 Rolf Schurter
- 👤 Henry Szczepanski
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 19:07
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/24; C07D213/28; C07D213/30; C07D213/60; C07D213/61; C07D213/72; C07D213/73; C07D213/76; C07D213/78; C07D213/79; C07D213/80; C07D213/84; C07D213/85; C07D239/00; C07D239/02; C07D239/24; C07D239/26; C07D239/28; C07D239/30; C07D251/00; C07D251/02; C07D251/12; C07D251/14; C07D251/16; C07D251/18; C07D251/20; C07D263/00; C07D263/02; C07D263/30; C07D263/32; C07D277/00; C07D277/02; C07D277/20; C07D277/22; C07D277/24; C07D285/00; C07D285/01; C07D285/02; C07D285/04; C07D285/08; C07D295/00; C07D295/04; C07D295/08; C07D295/084; C07D295/088; C07D307/00; C07D307/02; C07D307/34; C07D307/38; C07D307/40; C07D307/42; C07D333/00; C07D333/02; C07D333/04; C07D333/06; C07D333/14; C07D333/16
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
343 words
A phenylacetylene compound of the formula ##STR214## wherein A is an amino group of the formula ##STR215## each of R 1 and R 2 is hydrogen; C 3 -C 6 alkenyl; C 3 -C 6 alkynyl; C 3 -C 8 cycloalkyl; or C 1 -C 6 alkyl optionally substituted by halogen, hydroxy, C 1 -C 4 alkoxy, alkoxycarbonyl containing at most 5 carbon atoms, cyano or carboxyl; or, together with the nitrogen atom to which they are attached, R 1 and R 2 form a 5- or 6-membered saturated heterocyclic ring system containing altogether at most 2 hetero-atoms and which is optionally substituted by C 1 -C 3 alkyl; X.sup.⊖ is an anion; R is hydrogen; nitro; cyano; trifluoromethyl; C 1 -C 4 alkoxy; C 1 -C 4 alkylthio; --NR 5 R 6 ; CO--NR 7 R 8 ; --COOR 9 ; --CO--SR 10 ; halogen; --N 3 ; or C 1 -C 4 alkyl optionally substituted by C 1 -C 4 alkyl, hydroxy, cyano or --COOR 9 ; each of R 5 , R 7 , R 8 , R 9 and R 10 is hydrogen; C 1 -C 6 alkyl; C 3 -C 8 alkenyl; or C 3 -C 8 alkynyl; R 6 is hydrogen; C 1 -C 6 alkyl; C 3 -C 8 alkenyl; C 3 -C 8 alkynyl; --CO--R 11 ; --COOR 12 ; or --CO--NHR 13 ; in which R 11 , R 12 and R 13 have the same meanings as R 4 ; n is an integer from 1 to 4; and Z is heterocyclic radical selected from the group consisting of furanyl, thienyl, pyridyl, pyrimidinyl, thiazolyl and triazinyl, each of which is optionally substituted by one or more radicals having the same meaning as R, formyl, --SO 2 --NR 7 R 8 , --NH--NH 2 , --NHOH, --SO--R 9 , SO 2 --R 9 , ##STR216## COO.sup.⊖ M.sup.⊕ in which M.sup.⊕ is a sodium, potassium, calcium or magnesium cation, or C 2 -C 6 alkenyl which optionally substituted by nitro, cyano or --COOR 9 .
Claim 2
Dependent Claim
343 words
A phenylacetylene compound of the formula ##STR214## wherein A is an amino group of the formula ##STR215## each of R 1 and R 2 is hydrogen; C 3 -C 6 alkenyl; C 3 -C 6 alkynyl; C 3 -C 8 cycloalkyl; or C 1 -C 6 alkyl optionally substituted by halogen, hydroxy, C 1 -C 4 alkoxy, alkoxycarbonyl containing at most 5 carbon atoms, cyano or carboxyl; or, together with the nitrogen atom to which they are attached, R 1 and R 2 form a 5- or 6-membered saturated heterocyclic ring system containing altogether at most 2 hetero-atoms and which is optionally substituted by C 1 -C 3 alkyl; X.sup.⊖ is an anion; R is hydrogen; nitro; cyano; trifluoromethyl; C 1 -C 4 alkoxy; C 1 -C 4 alkylthio; --NR 5 R 6 ; CO--NR 7 R 8 ; --COOR 9 ; --CO--SR 10 ; halogen; --N 3 ; or C 1 -C 4 alkyl optionally substituted by C 1 -C 4 alkyl, hydroxy, cyano or --COOR 9 ; each of R 5 , R 7 , R 8 , R 9 and R 10 is hydrogen; C 1 -C 6 alkyl; C 3 -C 8 alkenyl; or C 3 -C 8 alkynyl; R 6 is hydrogen; C 1 -C 6 alkyl; C 3 -C 8 alkenyl; C 3 -C 8 alkynyl; --CO--R 11 ; --COOR 12 ; or --CO--NHR 13 ; in which R 11 , R 12 and R 13 have the same meanings as R 4 ; n is an integer from 1 to 4; and Z is heterocyclic radical selected from the group consisting of furanyl, thienyl, pyridyl, pyrimidinyl, thiazolyl and triazinyl, each of which is optionally substituted by one or more radicals having the same meaning as R, formyl, --SO 2 --NR 7 R 8 , --NH--NH 2 , --NHOH, --SO--R 9 , SO 2 --R 9 , ##STR216## COO.sup.⊖ M.sup.⊕ in which M.sup.⊕ is a sodium, potassium, calcium or magnesium cation, or C 2 -C 6 alkenyl which optionally substituted by nitro, cyano or --COOR 9 .
Claim 3
Dependent Claim
19 words
A phenylacetylene compound according to claim 1, wherein the radical --O--Q--A is in the 4-position to the ethynyl radical.
Claim 4
Dependent Claim
19 words
A phenylacetylene compound according to claim 1, wherein the radical --O--Q--A is in the 3-position to the ethynyl radical.
Claim 5
Dependent Claim
31 words
A compound according to claim 1, wherein the direct alkylene bridge between the bridge member O and the nitrogen atom of the group A consists of 2 or 3 carbon atoms.
Claim 6
Dependent Claim
17 words
A compound according to claim 1, wherein the radical Z is furanyl or thienyl, each optionally substituted.
Claim 7
Dependent Claim
19 words
A compound according to claim 1, wherein the radical Z is pyridyl, pyrimidinyl, thiazolyl or triazinyl, each optionally substituted.
Claim 8
Dependent Claim
16 words
A compound according to claim 1, wherein R 1 and R 2 are methyl or ethyl.
Claim 9
Dependent Claim
61 words
A compound according to claim 1, wherein the radical --O--Q--A is in the 4-position to the ethynyl radical, the direct chain between the bridge member O and the nitrogen atom of the group A consists of 2 to 3 carbon atoms, the radical Z is furanyl or thienyl, each optionally substituted and R 1 and R 2 are methyl or ethyl.
Claim 10
Dependent Claim
63 words
A compound according to claim 1, wherein the radical --O--Q--A is in the 3-position to the ethynyl radical, the direct chain between the bridge member O and the nitrogen atom of the group A consists of 2 or 3 carbon atoms, the phenyl, radical Z is phenyl, furanyl or thienyl, each optionally substituted and R 1 and R 2 are methyl or ethyl.
Claim 11
Dependent Claim
63 words
A compound according to claim 1, wherein the radical --O--Q--A is in the 4-position to the ethynyl radical, the direct chain between the bridge member O and the nitrogen atom of the group A consists of 2 or 3 carbon atoms, the radical Z is pyridyl, pyrimidinyl, thiazolyl or triazinyl, each optionally substituted and R 1 and R 2 are methyl or ethyl.
Claim 12
Dependent Claim
59 words
A compound according to claim 1, wherein the radical --O--Q--A is in the 3-position to the ethynyl radical, the direct chain between the bridge member O and the nitrogen atom consists of 2 or 3 carbon atoms, the radical Z is pyridyl, pyrimidinyl, thiazolyl or triazinyl, each optionally substituted and R 1 and R 2 are methyl or ethyl.
Claim 13
Dependent Claim
28 words
A compound according to claims 8, 9, 10 or 11 in which R is halogen, C 1 -C 4 alkyl, nitro or cyano, and n is 1. PG,66
Claim 14
Dependent Claim
1 words
1-[4-(4-Methoxyphenylethynyl)phenoxy]-2-diethylaminoethane.
Claim 15
Dependent Claim
1 words
1-[4-(4-Methoxyphenylethynyl)phenoxy]-2-diethylaminoethane.
Claim 16
Dependent Claim
1 words
1-[4-(4-Fluorophenylethynyl)phenoxy]-2-diethylaminoethane.
Claim 17
Dependent Claim
1 words
1-[4-(4-Fluorophenylethynyl)phenoxy]-2-diethylaminoethane.
Claim 18
Dependent Claim
5 words
1-[4-(2-Thienylethynyl)phenoxy]-2-diethylaminoethane according to claim 10.
Claim 19
Dependent Claim
26 words
A herbicidal composition comprising a herbicidally effective amount of at least one compound according to claim 1, 13 or 14, together with a suitable carrier therefor.
Claim 20
Dependent Claim
29 words
A method of controlling weeds, which method comprises applying thereto or to the locus thereof a herbicidally effective amount of a compound according to claim 1, 13 or 14.
Claim 21
Dependent Claim
22 words
A method according to claim 17 for selectively controlling weeds in crops of cultivated plants, which method comprises applying said compound postemergence.
Claim 22
Dependent Claim
13 words
A method according to claim 18, wherein the crop is cereals or maize.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-10-31 | 1987-05-02 | 1987-11-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-10-31 | 1991-05-02 | 1991-11-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-10-31 | 1995-05-02 | 1995-11-01 | $7700.00 | Window Closed / Lapsed |