Substituted 3-benzylpyrazoles and their use as herbicides

Details Substituted 3-benzylpyrazoles and their use as herbicides Substituted 3-benzylpyrazoles and their use as herbicides

1999-05-03

2002-09-17

Ramsuer, Robert W. (Department: 1626)

Plant protecting and regulating compositions

Plant growth regulating compositions

Abscission agent, defoliant, or desiccant

C504S282000, C548S366100

Reexamination Certificate

active

06451734

ABSTRACT:

this application is a 371 of PCT/EP97/06057 filed Nov. 3, 1997.
The present invention relates to novel substituted 3-benzylpyrazoles of the formula I
where:
R
1
is hydrogen, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkylsulfonyl or C
1
-C
4
-haloalkylsulfonyl;
R
2
is 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;
R
3
is hydrogen, cyano, nitro, halogen, C
1
-C
4
-alkyl or C
1
-C
4
-haloalkyl;
X
1
, X
2
, X
3
, X
4
and X
5
are each independently of one another a chemical bond or a methylene, ethylene or ethene-1,2-diyl chain or an oxymethylene or thiamethylene chain linked to the phenyl ring via the hetero atom, all chains being unsubstituted or substituted by one or two substituents selected in each case from the group consisting of cyano, halogen, C
1
-C
4
-alkyl and (C
1
-C
4
-alkoxy)carbonyl;
R
4
, R
5
, R
6
, R
7
and R
8
are each independently of one another hydrogen, nitro, cyano, halogen, —O—Y
1
—R
9
, —O—CO—Y
1
—R
9
, —N(Y
1
—R
9
) (Y
2
—R
10
), —N(Y
1
—R
9
)—SO
2
—Y
2
—R
10
, —N(SO
2
—Y
1
—R
9
)(SO
2
—Y
2
—R
10
), —N(Y
1
—R
9
)—CO—Y
2
—R
10
, —N(Y
1
—R
9
)(O—Y
2
—R
10
), —S—Y
1
—R
9
, —SO—Y
1
—R
9
, —SO
2
—Y
1
—R
9
, —SO
2—O—Y
1
—R
9
, —SO
2
—N(Y
1
—R
9
)(Y
2
—R
10
), —CO—Y
1
—R
9
, —C(═NOR
11
)—Y
1
—R
9
, —C(═NOR
11
)—O—Y
1
—R
9
, —C(═NOR
11
)—CO—O—Y
1
—R
9
, —CO—O—Y
1
—R
9
, —CO—S—Y
1
—R
9
, —CO—N(Y
1
—R
9
)(Y
2
—R
10
) or —CO—N(Y
1
—R
9
)(O—Y
2
—R
10
), where
Y
1
and Y
2
are each independently of each other a chemical bond or a methylene or ethylene chain which may in each case be unsubstituted or carry one or two C
1
-C
4
-alkyl substituents;
R
9
and R
10
are each independently of each other hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, C
1
-C
4
-alkoxy-C
1
-C
4
-alkyl, C
1
-C
4
-haloalkoxy-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
1
-C
4
-alkylsulfonyl-C
1
-C
4
-alkyl, C
1
-C
4
-haloalkylsulfonyl-C
1
-C
4
-alkyl, (C
1
-C
4
-alkyl)carbonyl-C
1
-C
4
-alkyl, (C
1
-C
4
-alkoxy)carbonyl-C
1
-C
4
-alkyl, di-(C
1
-C
4
-alkyl)aminocarbonyl-C
1
-C
4
-alkyl, C
3
-C
8
-cycloalkyl which may contain a carbonyl or thiocarbonyl ring member, phenyl or 3- to 7-membered heterocyclyl which may contain a carbonyl or thiocarbonyl ring member, the cycloalkyl, phenyl and heterocyclyl rings being in each case unsubstituted or substituted by one to four substituents selected in each case from the group consisting of cyano, nitro, amino, hydroxyl, carboxyl, halogen, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-alkylsulfonyl, (C
1
-C
4
-alkyl)carbonyl, (C
1
-C
4
-alkyl)carbonyloxy and (C
1
-C
4
-alkoxy)carbonyl, and R
11
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, C
3
-C
8
-cycloalkyl, phenyl or phenyl-C
1
-C
4
-alkyl;
and agriculturally or pharmaceutically useful salts of these compounds, but excluding 3-benzyl-1,5-dimethyl-1H-pyrazole, 3(5)-benzyl-5(3)-methyl-1H-pyrazole, 3(5)-benzyl-5(3)-trifluoromethyl-1H-pyrazole and 3(5)-(2-nitrobenzyl)-5(3)-methyl-1H-pyrazole.
The invention further relates to
the use of the compounds I and salts thereof as herbicides and/or for the desiccation/defoliation of plants,
herbicidal compositions and compositions for the desiccation and/or defoliation of plants which comprise the compounds I or salts thereof as active ingredients,
processes for preparing the compounds I and herbicidal compositions and compositions for the desiccation/defoliation of plants using the compounds I,
methods for controlling undesirable vegetation and for the desiccation/defoliation of plants using the compounds I,
intermediates of the formulae IIa, IIb and IIc, byproducts of the formula III and the salts of these compounds,
the use of the compounds I, IIa, IIb, IIc, III and salts thereof for preparing pharmaceutical preparations for treating diseases, in particular for lowering the blood sugar level,
pharmaceutical preparations comprising the compounds I, IIa, IIb, IIc and III or salts thereof as active substances, and also
processes for preparing the compounds IIa, IIb, IIc and III.
The 3-benzyl pyrazoles which a re excluded in claim
1
are already known from the following literature:
3-benzyl-1,5-dimethyl-1H-pyrazole from Chem. Heterocycl. Compd. (Engl. Transl.) 20 (1984), 189;
3(5)-benzyl-5(3)-methyl-1H-pyrazole from J. Org. Chem. 36 (1971), 4033;
3(5)-benzyl-5(3)-trifluoromethyl-1H-pyrazole from J. Fluorine Chem. 67 (1994), 83;
3(5)-(2-nitrobenzyl)-5(3)-methyl-1H-pyrazole from Chem. Ber. 61 (1928), 1118.
The 3-benzyl-5-hydroxypyrazoles and pyrazolones excluded in claim
13
are already known from the following literature:
5(3-chlorobenzyl)-1,2-dihydro-3H-pyrazol-3-one from Bioorg. Med. Chem. 4 (1996), 1401;
5-(2-aminobenzyl)-1,2-dihydro-3H-pyrazol-3-one from J. Heterocycl. Chem. 26 (1989), 71;
1,2-dihydro-5-(2-nitrobenzyl)-3H-pyrazol-3-one from Chem. Ber. 61 (1928), 1118;
the compounds where R
4
to R
8
are all hydrogen and simultaneously X
1
to X
5
are all simultaneously a chemical bond for example from Chem. Ber. 66 (1933), 1512 and Bull. Soc. Chim. Fr. 1969, 4159.
Some of the substituted 3-benzylpyrazoles of the formula I are—if the substituents are appropriately chosen—included in the general definition of compounds disclosed
in JP-A 64/13 050 in mixtures with aryloxyalkanoic acids as compositions for controlling plant growth,
in EP-A 468 372 as angiotensin II antagonists,
in EP-A 300 688 as cardiotonic agents,
in WO 96/20146 as nitrification inhibitors,
in WO 96/00218 as phosphodiesterase IV inhibitors,
in WO 96/03378 as ACAT inhibitors,
in WO 91/10140 as angiotensin II antagonist models,
in AU 8 783 175, EP-A 245 825 and AT 389 106 as 5-lipoxygenase inhibitors,
in WO 96/12706 as endothelin receptor antagonists,
in U.S. Pat. No. 4,649,025 in mixtures with 2 phosphonic acid derivatives as corrosion inhibitors and
in DE-A 39 27 483 as platelet activating factor antagonists.
In addition, some of the compounds of the formula I are included in the very wide definitions of pyrazoles whose preparation is described in DE-A 4 328 228, JP-A 06/345 728, EP-A 628 563, DE-A 3 918 979, DE-A 1 210 431, U.S. Pat. No. 3,254,093, EP-A 020 964, EP-A 045 394, EP-A 088 963 and EP-A 290 991.
Pyrazole intermediates whose general formula includes, if the substituents are chosen appropriately, 3-benzylpyrazoles of the type of the compounds I are mentioned
in EP-A 300 324 for preparing 4-acylpyrazoles,
in EP-A 328 020 as intermediates for catalysts in storage-stable epoxy phenol mixtures,
in EP-A 485 929 and WO 96/04273 for preparing angiotensin II receptor antagonists,
in EP-A 420 397, JP-A 63/166 879 and JP-A 01/085 974 for preparing photochromic data storage media,
in EP-A 087 780 for preparing sulfonylurea herbicides,
in EP-A 535 928 and EP-A 547 825 for preparing fungicides of the strobilurin type,
in WO 91/10 662 and EP-A 522 887 for preparing ACAT and thromboxane TxA inhibitors,
in EP-A 548 949 for preparing prostaglandin I2 receptor antagonists,
in DE-A 4 103 382 for preparing insecticidal cyclopropanecarboxamides,
in WO 95/01979 for preparing heteroazolyl heterocyclylalkane derivatives for treating neuropsychiatric disorders,
in EP-A 99 329 for preparing 1,3-dithiaheterocycles for treating disorders of the liver, of the respiratory tract and of the blood vessels,
in EP-A 230 110 for preparing compounds which are, inter alia, supposed to have a cardiotonic and hypoglycemic action,
in JP-A 01/190 670 and JP-A 63/112 566 for preparing insecticidal pyrimidinones,
in DE-A 3 830 238 and EP-A 192 060 for preparing insecticides of the nitroguanidine type,
in EP-A 363 796 for preparing monoamine oxidase inhibitors and
in EP-A 181 163 for preparing histamine H2 receptor antagonists.
It is an object of the present invention to provide novel herbicidally active compounds which allow better selective

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