Substituted aromatic phoshonic acid derivatives

Details Substituted aromatic phoshonic acid derivatives Substituted aromatic phoshonic acid derivatives

1998-08-04

2001-01-16

Shah, Mukund J. (Department: 1624)

Organic compounds -- part of the class 532-570 series

Organic compounds

Four or more ring nitrogens in the bicyclo ring system

C544S066000, C504S243000

Reexamination Certificate

active

06175007

ABSTRACT:

The present invention relates to novel substituted aromatic phosphonic acid derivatives of the formula I
where the variables have the following meanings:
Eth is 1,2-ethynediyl or an ethane- or ethene-1,2-diyl chain, each of which can be unsubstituted or have attached to it one or two of the following substituents: halogen, cyano, carboxyl, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, (C
1
-C
4
-alkoxy)carbonyl and/or di(C
1
-C
4
-alkyl)amino, it being possible for the ethane-1,2-diyl chain, if desired, additionally to have attached to it a hydroxyl, amino or C
1
-C
4
-alkylamino group;
Y
1
is oxygen or sulfur;
Y
2
is oxygen, sulfur or —N(R
6
)—;
Y
3
is oxygen, sulfur or —N(R
7
)—;
R
1
, R
2
, R
6
and R
7
independently of one another are hydrogen,
C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, hydroxy-C
1
-C
4
-alkyl, cyano-C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy-C
1
-C
4
-alkyl, C
1
-C
4
-haloalkoxy-C
1
-C
4
-alkyl, C
3
-C
4
-alkenyloxy-C
1
-C
4
-alkyl, C
3
-C
4
-alkynyloxy-C
1
-C
4
-alkyl, C
3
-C
8
-cycloalkoxy-C
1
-C
4
-alkyl, amino-C
1
-C
4
-alkyl, C
1
-C
4
-alkylamino-C
1
-C
4
-alkyl, di(C
1
-C
4
-alkyl)amino-C
1
-C
4
-alkyl, C
1
-C
4
-alkylthio-C
1
-C
4
-alkyl, C
1
-C
4
-haloalkylthio-C
1
-C
4
-alkyl,
C
3
-C
4
-alkenylthio-C
1
-C
4
-alkyl, C
3
-C
4
-alkynylthio-C
1
-C
4
-alkyl, C
1
-C
4
-alkylsulfinyl-C
1
-C
4
-alkyl, C
1
-C
4
-haloalkylsulfinyl-C
1
-C
4
-alkyl, C
3
-C
4
-alkenylsulfinyl-C
1
-C
4
-alkyl, C
3
-C
4
-alkynyl-sulfinyl-C
1
-C
4
-alkyl, C
1
-C
4
-alkylsulfonyl-C
1
-C
4
-alkyl, C
1
-C
4
-haloalkylsulfonyl-C
1
-C
4
-alkyl, C
3
-C
4
-alkenylsulfonyl-C
1
-C
4
-alkyl, C
3
-C
4
-alkynylsulfonyl-C
1
-C
4
-alkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-haloalkenyl, cyano-C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, C
3
-C
6
-haloalkynyl, cyano-C
3
-C
6
-alkynyl, hydroxycarbonyl-C
1
-C
4
-alkyl, (C
1
-C
4
-alkoxy)carbonyl-C
1
-C
4
-alkyl, (C
1
-C
4
-alkyl-thio)carbonyl-C
1
-C
4
-alkyl, aminocarbonyl-C
1
-C
4
-alkyl, (C
1
-C
4
-alkyl)aminocarbonyl-C
1
-C
4
-alkyl, di(C
1
-C
4
-alkyl)amino-carbonyl-C
1
-C
4
-alkyl,
C
3
-C
8
-cycloalkyl, C
3
-C
8
-cycloalkyl-C
1
-C
4
-alkyl, phenyl, phenyl-C
1
-C
4
-alkyl or
3- to 7-membered heterocyclyl or heterocyclyl-C
1
-C
4
-alkyl, it being possible for all heterocycles, if desired, to contain a carbonyl or thiocarbonyl ring member,
and it being possible for all cycloalkyl, phenyl and heterocyclyl rings to be unsubstituted or to have attached to them one to four substituents, in each case selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, carboxyl, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-haloalkylthio, C
1
-C
4
-alkylsulfonyl, C
1
-C
4
-haloalkylsulfonyl, (C
1
-C
4
-alkyl)carbonyl, (C
1
-C
4
-haloalkyl)carbonyl, (C
1
-C
4
-alkoxy)carbonyl, (C
1
-C
4
-alkyl)carbonyloxy, (C
1
-C
4
-haloalkyl)carbonyloxy and di(C
1
-C
4
-alkyl)amino, or
R
1
and R
2
or R
1
and R
6
and/or R
2
and R
7
in each case together form a 1,2-ethanediyl, 1,3-propylene, tetramethylene, pentamethylene or ethyleneoxyethylene chain which, if desired, can be substituted by one to four C
1
-C
4
-alkyl and/or one or two (C
1
-C
4
-alkoxy)carbonyl groups, or
R
1
and R
2
together are 1,2-phenylene which can be unsubstituted or have attached to it one to three substituents, in each case selected from the group consisting of cyano, nitro, halogen, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy and C
1
-C
4
-haloalkoxy;
R
3
is cyano, halogen, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy or C
1
-C
4
-haloalkoxy;
R
4
is hydrogen or halogen;
R
5
is one of the following heterocycles &PHgr;
1
to &PHgr;
20
:
where
R
8
is hydrogen, amino, C
1
-C
4
-alkyl or C
1
-C
4
-haloalkyl;
R
9
is cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkylsulfonyl or C
1
-C
4
-haloalkylsulfonyl;
R
10
is C
1
-C
4
-alkyl or C
1
-C
4
-haloalkyl;
R
11
is cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-haloalkylthio, C
1
-C
4
-alkylsulfinyl, C
1
-C
4
-haloalkylsulfinyl, C
1
-C
4
-alkylsulfonyl or C
1
-C
4
-haloalkylsulfonyl, or
R
10
and R
11
together with the ring atoms linking them are a 5- to 7-membered heterocycle which has one or two hetero atoms and which can be unsubstituted or have attached to it one or two C
1
-C
4
-alkyl radicals;
R
12
is hydrogen, cyano, halogen, C
1
-C
4
-alkyl or C
1
-C
4
-haloalkyl;
Y
4
is oxygen, sulfur or methylene;
R
13
, R
14
, R
25
, R
26
, R
27
, R
28
, R
30
and R
31
independently of one another are hydrogen or C
1
-C
4
-alkyl, or
R
13
and R
14
together with the ring atoms linking them are a 5- to 7-membered carbo- or heterocyclic ring, it being possible for the ring, if desired, additionally to have attached to it one or two halogen and/or C
1
-C
4
-alkyl radicals or a further, fused 3- to 6-membered carbo- or heterocyclic ring;
R
15
and R
16
independently of one another are hydrogen, halogen, C
1
-C
4
-alkyl or C
1
-C
4
-haloalkyl, or
R
15
and R
16
together with the ring atoms linking them are a 5- to 7-membered carbo- or heterocyclic ring which, if desired, can additionally have attached to it one or two C
1
-C
4
-alkyl radicals;
R
17
is halogen or C
1
-C
4
-alkyl;
R
18
, R
33
and R
35
independently of one another are halogen;
R
19
, R
20
, R
29
, R
37
, R
38
, R
39
, R
40
, R
41
, R
42
, R
44
, R
55
and R
57
independently of one another are hydrogen, C
1
-C
4
-alkyl or C
1
-C
4
-halo-alkyl, or
R
19
and R
20
and/or R
39
and R
40
and/or R
41
and R
42
and/or R
55
and R
56
together with the ring atoms linking them are a 5- to 7-membered ring which, if desired, can additionally have attached to it one or two C
1
-C
4
-alkyl or C
1
-C
4
-haloalkyl radicals;
Y
5
, Y
6,
Y
7
, Y
9
and Y
10
independently of one another are oxygen or sulfur;
Z
1
, Z
2
, Z
3
and Z
4
independently of one another are nitrogen or CH;
R
21
and R
22
and/or R
23
and R
24
and/or R
53
and R
54
together with the ring atoms linking them are a 5- to 7-membered ring which, if desired, can additionally have attached to it one or two C
1
-C
4
-alkyl radicals;
R
32
, R
34
, R
48
, R
49
and R
52
independently of one another are hydrogen, C
1
-C
4
-alkyl, C
3
-C
6
-cycloalkyl or C
1
-C
4
-haloalkyl;
Y
8
is oxygen or ═NH;
R
36
is hydrogen, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl or C
1
-C
4
-haloalkoxy;
R
43
is C
1
-C
4
-alkyl; and
R
45
, R
46
, R
47
, R
50
and R
51
independently of one another are C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl or C
3
-C
6
-cycloalkyl,
and the agriculturally useful salts of the compounds I,
with the exception of those compounds I where R
4
is hydrogen and R
5
is &PHgr;
2
.
Furthermore, the invention relates to
the use of the compounds I as herbicides or for the desiccation/defoliation of plants,
herbicidal compositions and compositions for the desiccation/defoliation of plants which comprise the compounds I as active substances,
processes for the preparation of the compounds I and of herbicidal compositions and compositions for the desiccation/defoliation of plants using the compounds I,
methods of controlling undesirable vegetation and of desiccating/defoliating plants using the compounds I,
intermediates of the formulae XXVIII, XXXI, XXXII, XXXIIIa, XXXV and XL and processes for their preparation.
The herbicidal activity of diethyl 1-chloro-2-[2,4-dichloro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenyl]ethylphosphonate has already been mentioned by G. Theodoridis, J. T. Bahr, B. L. Davidson, S. E. Hart, F. W. Hotzman, K. M. Poss & S. F. Tutt in ACS Symp. Ser. 584, 90 (1995).
JP 03/151 367 describes 3-phenylpyrazoles of the formula
where R
57
is, inter alia, dialkoxyphosphinylalkyl as being herbicides.
WO 95/32188 furthermore discloses herbicidally active 3-phenylpyrazoles of the formula
where the alkyl/haloalkyl substituents are in each case C
1
-C
4
and
R
58
is hydrogen, nitro, halogen, carboxyl or an ester or acid amide radical and
R
59
is —CH
2
—CH
2
—P(O)(OR
60
)
2
or —CH═CH—P(O)(

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