Substituted diphenyl ethers and herbicidal composition containing them 机翻标题: 暂无翻译,请尝试点击翻译按钮。

公开号/公开日
GB1507159 A 1978-04-12 [GB1507159] / 1978-04-12
申请号/申请日
1975GB-0030410 / 1975-07-17
发明人
申请人
ISHIHARA MINING & CHEMICAL
主分类号
IPC分类号
A01N-039/02;A01N-043/40;A01N-043/647;A01N-043/653;A01N-047/34;A01N-053/08;C07C-051/367;C07C-051/41;C07C-059/68;C07C-059/70;C07C-069/65;C07C-069/712;C07C-069/76;C07C-233/00;C07C-233/02;C07C-275/50;C07C-327/22;C07D-213/64;C07D-213/75;C07D-249/14;C07D-295/18
摘要
(GB1507159)
1507159 Substituted diphenyl ethers and herbicidal compositions containing them ISHIHARA SANGYO KAISHA Ltd 17 July 1975 [17 July 1974 (2) 14 Oct 1974] 30410/75 Heading C2C The invention comprises an α-[4-(4-trifluoromethylphenoxy)phenoxy]alkanecarboxylic acid or a derivative thereof represented by the general Formula (I) wherein R is a (C 1 -C 6 ) alkyl group; R<SP>1</SP> is a hydroxy group, a (C 1 -C 9 ) alkoxy group; a (C 1 -C 4 ) alkoxy (C 1 -C 4 ) alkoxy group; a (C 1 -C 4 ) alkoxy (C 1 -C 4 ) alkoxy (C 1 -C 4 ) alkoxy group; a (C 1 -C 4 ) alkylthio group; a (C 2 -C 4 ) alkenyloxy group; a (C 2 -C 4 ) alkynyloxy group; a cyclohexyloxy group substituted with a methyl group; a phenoxy group substituted with one or more of a chlorine atom, a methyl group or a methoxy group ; aphenylthio group substituted with a chlorine atom; a benzyloxy group; an amino group; a mono- (C 1 -C 4 ) alkylamino group; an -NHCH 2 COOZ group in which Z is a hydrogen atom, a cation or a (C 1 -C 4 ) alkyl group; a di-(C 1 -C 4 ) alkylamino group; a benzylamino group; a hydrazino group; an N<SP>1</SP>,N<SP>1</SP>-di-(C 1 -C 4 ) alkylhydrazino group; an anilino group; an anilino group substituted with one or more of a halogen atom, a methyl group, an ethyl group, a methoxy group or a trifluoromethyl group; a N-methyl- N-phenyl amino group; a carbamoylamino group; an N<SP>1</SP>,N<SP>1</SP>-di-(C 1 -C 4 ) alkyl carbamoylamino group; an N-3,4-dichlorophenyl-N<SP>1</SP>,N<SP>1</SP>- di-(C 1 -C 4 ) alkyl carbamoylamino group; a (C 1 -C 6 ) acylamino group; an N-3,4-dichlorophenyl - N - (C 1 -C 6 ) acylamino group, a pyridylamino group; a pyridylamino group in which the pyridyl moiety thereof is substituted with a methyl group ; a triazolylamino group; a morpholino group; an -OM group in which M is a cation; or a halogen atom; and n is 0 or 1. 
These compounds may be obtained by first condensing a p-halo-α,α,α-trifluorotoluene of formula wherein Hal is a halogen atom, and n is as defined above and a p-substituted phenol of formula wherein Y is a hydroxy group, a C 1-5 alkoxy group or an -OCHR-COR<SP>3</SP> in which R is as defined above, and R<SP>3</SP> is a hydroxy group, a C 1-9 alkoxy group or an amino group, at at least 100‹ C. to form a 4-trifluoromethyl-41-substituted diphenyl ether of formula wherein Y and n are as defined above and, when Y is a C 1-5 alkoxy group or a hydroxy group, condensing the compound of Formula IV with an α-haloalkanecarboxylic acid or a derivative thereof of formula wherein R, R<SP>3</SP> and Hal are as defined above, at 40‹ to 120‹C., in the presence of an alkaline material, to form a compound of formula wherein R, R<SP>3</SP> and n are as defined above, and, if necessary, converting the R<SP>3</SP> moiety of the compound of Formula V to R<SP>1</SP> wherein R<SP>1</SP> is as defined above. 
Herbicidal compositions comprise as an active ingredient a compound of Formula I in association with an inert carrier or diluent.
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地址
代理人
代理机构
优先权号
1974JP-0082403 1974-07-17 1974JP-0082404 1974-07-17 1974JP-0117047 1974-10-14
主权利要求
(GB1507159)
1. WHAT WE CLAIM IS: 5 I A compound having the general formula (I) Cn R O CF 3 O ol 01 H CRI wherein R is a (C,-C 6)alkyl group; R' is a hydroxy group, a (C,-C 9) alkoxy group; a (C, C 4)alkoxy(C,-C 4)alkoxy group; a (Cl-C 4)alkoxy(CI-C 4) alkoxy(Cl C 4)alkoxy group; a (C,-C 4)alkylthio group; a (C 2-C 4)alkenyloxy group; a 10 (C 2-C 4)alkynyloxy group; a cyclohexyloxy group substituted with a methyl group; a phenoxy group substituted with one or more of a chlorine atom, a methyl group or a methoxy group; a phenylthio group substituted with a chlorine atom; a benzyloxy group; an amino group; a mono-(C 1-C 4)alkylamino group; an -NICIH 2 COOZ group in which Z is a hydrogen atom, a cation or a (C,-C 4) alkyl 15 group; a di-(C,-C 4)alkylamino group; a benzylamino group; a hydrazino group; an N',N'-di(C, C 4)alkylhydrazino group; an anilino group; an anilino group substituted with one or more of a halogen atom, a methyl group, an ethyl group, a methoxy group or a trifluoromethyl group; a N-methyl-N-phenyl amino group; a carbamoylamino group; an N',N'-di-(C C 4)alkyl carbamoylamino group; an N3,4-dichlorophenyl-N',N'-di-(C C 4)alkyl carbamoylamino group, a (C, C 6)acylamino group; an N-3,4-dichlorophenyl-N-(C,-C 6)acylamino group; a 5 pyridylamino group; a pyridylamino group in which the pyridyl moiety thereof is substituted with a methyl group; a triazolylamino group; a morpholino group; an -OM group in which M is a cation; or a halogen atom; and N is 0 or 1.
2. A compound as claimed in claim 1, having the general formula ( 1 ') RO CF 3 O t OCH QH ( 1 t) 10 wherein R is (C 2-C 4)alkyl group.
3. A compound as claimed in claim 1, having the general formula ( 1 ") x CC 3 O CF 3 / O O HC CR 1 (II") wherein X is a hydrogen atom or a chlorine atom and R' is as defined in claim 1.
4. A compound as claimed in claim 3, wherein X is a hydrogen atom; and R' is 15 a hydroxy group, a (Cl-C 9)alkoxy group, or an -OM group in which M is a cation.
5. A compound as claimed in claim 3, wherein X is a hydrogen atom; and R' is a (C C 4)alkoxy (Ct C 4)alkoxy group; a (C,-C 4)alkoxy-(C,-C 4)alkoxy(C,C 4)alkoxy 'group; a (C C 4)alkylt-hio group; a (C 2-C 4)alkenyloxy group; a 20 (C 2-C 4)alkynyloxy group; a cyclohexyloxy group substituted with a methyl group, a phenoxy group substituted with one or more of a chlorine atom, a methyl group or a methoxy group; phenylthio group substituted with a chlorine atom; a benzyloxy group; an -NHCH 2 COOZ group in which Z is a hydrogen atom, a cation or a (C,-C 4)alkyl group; a di-(C,-C 4)alkylamino group; a benzylamino 25 group; an N',N'-di-(C,-C 4)alkylhydrazino group; an N-methyl-Nphenylamino group; a carbamoylamino group; an N',N'-di-(C,-C 4)alkyl carbamoylamino group; an N-3,4-dichlorophenyl-N',N'-di-(C,-C 4)alkyl carbamoylamino group, a (C,-C 6)acylamino group; an N-3,4-dichlorophenyl-N-(C,-C 6)acylamino group; a pyridylamino group; a pyridylamino group in which the pyridyl moiety thereof is 30 substituted with a methyl group; a triazolylamino group; a morpholino group: or a halogen atom.
6. A compound as claimed in claim 5, wherein R' is a (C, C 4)alkoxy(Cl-C 4)alkoxy group; a (C,-C 4)alkoxy(C C 4)alkoxy(C C 4)alkoxy group; a (C,-C 4)alkylthio group; a (C 2-C 4)alkenyloxy group; a (C 2-C 4) alkynyloxy group; 35 or a benzyloxy group.
7. A compound as claimed in claim 6, wherein R' is an n-butoxyethoxy group, an ethoxyethoxyethoxy group, an ethylthio group, an allyloxy group, a 2propynyloxy group, or a benzyloxy group.
8. Methyl a-l 4-( 4-trifluoromethylphenoxy)phenoxylpropionate 40 9 Ethyl a-l 4-( 4-trifluoromethylphenoxy)phenoxylpropionate.
Sodium a-l 4-( 4-trifluoromethylphe N oxy)phenoxylpropionate.
11. A herbicidal composition comprising a herbicidally effective amount of at least one compound as claimed in any preceding claim as an active ingredient and an agriculturally acceptable adjuvant 45 12 A method for controlling noxious weeds in the presence of cultivated crops which comprises applying a herbicidally effective amount of a herbicidal composition as claimed in claim 12 to an upland area where the cultivated crops are growing.
13. A method of selectively controlling gramineous weeds in the presence of 50 broad-leafed crops which comprises applying a herbicidally effective amount of a herbicidal composition as claimed in claim 11 to an upland area where the broadleafed crops are growing, thereby to kill gramineous weeds selectively by withering.
14. A process for preparing a compound having general formula (I) 55 1,507,159 Ctn R O 1,507,159 30 CF1 ( 1 Cm wherein R, R' and N are as defined in claim 1, which comprises first condensing a p-halo-,a, a'-trifluorotoluene having the formula (II) Cmn CF 3 Ha (II) wherein Hal is a halogen atom, and N is as defined above and a psubstituted 5 phenyl having the formula (III) Ho-( -Y (III) wherein Y is a hydroxy group, a (C,-C 5)alkoxy group or an R O I i 1 -OCHCR 3 group, in which R is as defined above, and R 3 is a hydroxy group, a (C,C 9)alkoxy 10 group, or an amino group, at at least 100 C in the presence of an alkaline material to form a 4 otrifluoromethyl-4 '-substituted diphenyl ether having the formula (IV) Cln C Fy Ojj Y (IV) wherein Y and N are as defined above, and, when Y is a (Cl-Cs)alkoxy group or a hydroxy group, condensing the 4-trifluoromethyl-4 '-substituted diphenyl ether 15 having'the formula (IV) and an a-haloalkanecarboxvlic acid or a derivative thereof having the formula (VI) R O I i (VI) Hal-CHCR 3 wherein R, R 3 and Hal are as defined above, at 40 C to 120 C in the presence of an alkaline material, thereby to form a compound having the formula (V) 20 Can R O Cf-OF\\ 1 13 (V) 6 xx OC wherein R, R 3 and N are as defined above, and, if necessary, converting the R 3 moiety of the compound of formula (V) to R' wherein R' is as defined above.
A process as claimed in claim 14, which comprises condensing a p-haloa, ao-trifluorotoluene having the formula (II) 25 Cln CF 3 -6 -Hal (II) CF 3-Hn wherein Hal and N are as defined above, with a p-hvdroxyphenoxyalkanecarboxylic acid or a derivative thereof having the formula (VII) R O 3 I -1 (VII) HO O CN CR 3 1,507,159 wherein R and R 3 are as defined above, in the presence of an alkaline material to form a compound having the formula (V) Can R O CF 3 t -m Ill OC (V) wherein R, R 3 and N are as defined above, and if necessary, converting the R 3 moiety of the compound of the formula (V) to R' wherein R' is as defined above 5 16 A process as claimed in claim 14, which comprises condensing a p-haloa, ar, a-trifluorotoluene having the formula (II) Cln CF 3 -6 Hal (II) wherein Hal and N are as defined above, with hydroquinone in the present of an alkaline material to form a 4-trifluoromethyl-4 '-hydroxydiphenyl ether having the 10 formula (VIII) Cmn C Fj 3 O -t 3-OH (VIII) wherein N is as defined above, further condensing the compound of the formula (VIII) with an cr-haloalkanecarboxylic acid or a derivative thereof having the formula (VI) 15 R O ¦,I (VI) Hal-CHCR 3 wherein Hal and R 3 are as defined above, in the presence of an alkaline material to form a compound having the formula (V) Cn R O CF 3 t 6 O 9 F\OCCR 3 wherein R, R 3 and N are as defined above, and if necessary, converting the R 3 20 moiety of the compound of the formula (V) to R', wherein R' is as defined above.
17. A process as claimed in claim 14, which comprises condensing a p-halo(J,(o, a-trifluorotoluene having the formula (II) C/n CF 5 -6 Hal(II) CF 3 - o wherein Hal and N are as defined above, with a hydroquinone monoalkyl ether 25 having the formula (IX) Woe\ O alkj (IX) wherein "alkyl" is an alkyl group, in the presence of an alkaline material to form a 4-trifluoromethyl-4 '-alkoxydiphenyl ether having the formula (X) C Ln (X) 30 CF 3- O j O,k wherein "alkyl" and N are as defined above, dealkylating the 4trifluoromethyl-4 'alkoxydiphenyl ether having the formula (X) to form a 4-trifluoromethyl-4 'hydroxydiphenyl ether having the formula (VIII) 1,507,159 Cmn CF 3- O -O H (VIII) wherein N is as defined above, condensing the compound having the formula (VIII) with an a-haloalkanecarboxylic acid or a derivative thereof having the formula (VT) R O 1 J (VI) 5 Hal-CHCH 3 wherein R and R 3 are as defined above, in the presence of an alkaline material to form a compound having the formula (V) Cin R 0 CF 3 &amp; 40 e\O CIHR 3 (V) Cn wherein R, R 3 and N are as defined above, and if necessary, converting the R 3 moiety of the compound of the formula (V) to R', wherein R' is as defined above 10 18 A process as claimed in any one of claims 14 to 17, wherein said alkaline material in the first and second condensations is an alkali metal hydroxide or an alkali metal carbonate.
19. A process as claimed in any one of claims 15 to 19, wherein said first condensation is carried out for 1 to 20 hours 15 A process as claimed in any one of claims 14, 16 and 17, wherein said second condensation is carried out for 0 5 to 10 hours.
21. A process as claimed in any one of claims 14 to 20, wherein said first condensation is carried out in the presence of an aprotic-polar solvent.
22. A process as claimed in any one of claims 14 to 21, wherein said second 20 condensation is carried out in the presence of a ketone solvent.
23. A process as claimed in claim 14, wherein Y is an alkoxy group and said process includes dealkylating the alkyl moiety of said alkoxy group at a temperature of 150 to 200 C for 5 to 10 hours using pyridine hydrochloride as a dealkylating agent prior to the condensing with the crhaloalkanecarboxylic acid or 25 derivative thereof having the formula (VI).
24. A process as claimed in claim 14, wherein Y is an alkoxy group and said process includes dealkylating the alkyl moiety of said alkoxy group in the presence of acetic acid or acetic anhydride at a temperature near the boiling point of said acetic acid or acetic anhydride for 5 to 10 hours using a hydrohalic acid as a 30 dealkylating agent prior to the condensing with the arhaloalkanecarboxylic acid or derivative thereof having the formula (VI).
25. A process for the preparation of the compound of formula (I), substantially as hereinbefore described in any one of Preparation Examples 1 to 8.
26. A herbicidal formulation substantially as hereinbefore described in any 35 one of Formulation Examples I to 6.
MARKS &amp; CLERK, Alpha Tower, ATV Centre, Birmingham Bl ITT.
Agents for the Applicants.
Printed for Her Majesty's Stationery Office by the Courier Press, Leamington Spa, 1978.
Published by the Patent Office, 25 Southampton Buildings, London, WC 2 A l AY, from which copies may be obtained.
1. 507,159
法律状态
(GB1507159)
LEGAL DETAILS FOR GB1507159

Actual or expected expiration date=1984-03-14   
Legal state=DEAD   
Status=LAPSED 



Event publication date=1975-07-17 
Event code=GB/APP 
Event indicator=Pos 
Event type=Examination events 
Application details

Application country=GB GB3041075 
Application date=1975-07-17 
Standardized application number=1975GB-0030410 



Event publication date=1978-04-12 
Event code=GB/A 
Event indicator=Pos 
Event type=Event indicating In Force 
Patent specification

Publication country=GB 
Publication number=GB1507159 
Publication stage Code=A 
Publication date=1978-04-12 
Standardized publication number=GB1507159 



Event publication date=1978-08-23 
Event code=GB/PS 
Event indicator=Pos 
Event type=Event indicating In Force 
Patent sealed



Event publication date=1979-01-24 
Event code=GB/433D 
Event type=Opposition and reexamination events 
Application made for revocation (sect. 33/1949)



Event publication date=1979-10-31 
Event code=GB/SPA 
Event type=Examination events 
Amended specification published



Event publication date=1984-03-14 
Event code=GB/PCNP 
Event indicator=Neg 
Event type=Event indicating Not In Force 
Patent ceased through non-payment of renewal fee
专利类型码
A
国别省市代码
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