Defoliant

Details Defoliant Defoliant

2000-03-09

2002-09-03

Clardy, S. Mark (Department: 1616)

Plant protecting and regulating compositions

Plant growth regulating compositions

Plural active ingredients

C504S130000, C504S134000, C504S136000, C504S139000

Reexamination Certificate

active

06444613

ABSTRACT:

The invention relates to the field of defoliants, in particular thidiazuron-comprising mixtures, and their use in crops of cotton.
Thidiazuron has been known for some time as a defoliant, in particular for use in crops of cotton (see, for example, “The Pesticide Manual”, 11th edition, British Crop Protection Council, Farnham 1997).
The use of thidiazuron in mixtures has also been described, see, for example, DE-A2646712.
However, since the economical and ecological demands placed on modem defoliants are constantly being raised, for example with respect to effect, application rate, residues, toxicity and favorable manufacturing, there exists the permanent task of developing, for example by combining known active ingredients, novel defoliants which offer, at least in some areas, advantages compared with the known compounds.
Surprisingly, it has now been found that thidiazuron in mixtures with certain herbicides which inhibit the activity of the enzyme protoporphyrinogen-(IX) oxidase (PPO inhibitors) has synergistic effects.
EP-A 0 412 364 and DE-A 39 05 916 describe or propose diphenyl ether or N-phenyl-3,4,5,6-tetrahydrophthalimide derivatives in mixtures with thidiazuron.
However, a connection between the defoliant effect and the herbicidal mechanism of action of the compounds is not established.
EP-A 0 787 429 describes 3-substituted phenylpyrazoles as defoliants, possible mixtures with thidiazuron are not mentioned.
Smith et al. (1996 Beltwide Cotton Conference, Abstracts, p. 1159) report about fluthiacet-methyl as defoliant, without discussing mixtures with other active ingredients.
DE-A 198 34 629 describes a mixture of thidiazuron and fluthiacet-methyl for use as a herbicide.
The present invention accordingly provides the use of a mixture comprising
(A) thidiazuron or thidiazuron and diuron and
(B) one or more PPO inhibitors of the formula (I)
W—V  (I),
 for effecting leaf abscission of plants,
where the symbols in the formula (I) have the following meanings:
W is a cyclic group W-1 to W-23
V is one of the groups V-1 to V-11
R
1
is hydrogen or halogen;
R
2
is halogen, alkyl, alkoxy, haloalkoxy or haloalkyl;
R
3
is hydrogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkyl-S(O)
n
—, dialkylamino, alkylamino, amino or halogen;
R
4
is hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, formyl, alkyl-CO— or amino;
R
5
is hydrogen, halogen, alkyl, haloalkyl or nitro;
R
6
is hydrogen, alkyl or haloalkyl;
R
7
is hydrogen, alkyl or haloalkyl;
R
8
is hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl or haloalkynyl;
R
9
is hydrogen, alkyl, halogen, alkoxy, haloalkyl, haloalkoxy, alkoxycarbonyl, haloalkoxycarbonyl or amino;
R
10
is hydrogen, alkyl, halogen, alkoxy, haloalkyl, haloalkoxy, alkoxycarbonyl, haloalkoxycarbonyl or amino;
R
11
is hydrogen or alkyl;
R
12
is hydrogen, alkyl or halogen;
R
13
is hydrogen, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, cyano, nitro, amino, alkylamino, dialkylamino, alkoxycarbonyl, —(C═O)NH
2
, —(C═S)NH
2
, hydroxyl, acyloxy, substituted phenyl, substituted phenoxy, substituted benzyl or substituted benzyloxy;
R
14
is hydrogen, alkyl, haloalkyl, alkoxyalkyl, haloalkoxyalkyl, alkenyl, haloalkoxyalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy, halogen, —O—COR
15
, —OH, —S(O)
n
R
15
, —COR
17
, —CONR
18
R
19
, —CO
2
R
20
, —(CR
6
R
7
)
n
—CO
2
R
20
, —CR
21
═CR
22
CO
2
R
20
, —CN, —CR
11
(X
1
R
23
)(X
2
R
24
), —NR
11
—(CR
6
R
7
)
n
—CO
2
R
20
, —O—(CR
6
R
7
)
n
—CO
2
R
20
, —S(O)
n
—CR
21
═CR
22
—C(O)NR
16
R
17
, —(NR
6
R
7
)
n
CONR
16
R
17
—(CR
6
R
7
)
n
—CO
2
R
20
, —NO
2
, —NR
16
R
17
, —NR
24
SO
2
R
15
or —NR
23
COR
15
;
R
15
is hydrogen, M, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl or halogen;
R
16
is hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl or halogen;
R
17
is hydrogen, OH, OM, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxyalkyl or haloalkoxyalkyl;
R
18
is hydrogen, alkyl, alkoxy, alkenyl, haloalkenyl, alkynyl or haloalkynyl;
R
19
is hydrogen, alkyl, alkoxy or
R
18
and R
19
together with the nitrogen atom form a 5-, 6- or 7-membered ring which may be interrupted by oxygen or sulfur;
R
20
is hydrogen, M, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxyalkyl, haloalkoxyalkyl or —(CR
6
R
7
)
n
—CO
2
R
15
;
R
21
is hydrogen, alkyl, halogen or CN;
R
22
is hydrogen, alkyl, halogen or CN;
R
23
is hydrogen or alkyl;
R
24
is hydrogen, alkyl or
R
23
and R
24
together are a substituted or else unsubstituted 5-, 6- or 7-membered cyclic acetal or thioacetal;
R
25
is hydrogen, alkyl, alkoxy, alkenyl, haloalkenyl, alkynyl, haloalkynyl, carbamoyl or thiocarbamoyl;
M is an alkali metal, alkaline earth metal or ammonium ion;
X
1
is identical or different and is C-R
5
or N;
X
2
is identical or different and is CR
2
R
6
, O, —S(O)
n
— or NR
25
;
Y
1
is O or S;
Y
2
is O or S;
n, m are 0, 1 or 2;
U
1
is O, S(O)
n
, NR
23
or CR
9
R
10
;
U
2
is S(O)
n
, CR
9
R
10
or C═O;
T is CR
2
R
6
, NH or NR
2
.
The invention also provides defoliants or compositions for effecting leaf abscission of plants, comprising one of the mixtures described above, and a process for effecting the leaf abscission of plants, where the plants are treated with one of the abovementioned mixtures or a composition according to the invention.
The invention furthermore provides the abovementioned mixtures themselves, except for mixtures of thidiazuron or thidiazuron and diuron and fluthiacet-methyl.
The abovementioned mixtures are suitable in particular for use in crops of cotton, for example by rapid and/or increased activity or reduced application rates.
For the purpose of the invention, the term defoliant is synonymous with “desiccant” and also embraces the known growth-regulating effect of thidiazuron and of mixtures comprising thidiazuron.
The abovementioned mixtures preferably comprise synergistically effective amounts of the component (A) and synergistically effective amounts of the component (B).
In the above formula (I), “halogen” is to be understood as a fluorine, chlorine, bromine or iodine atom;
the term “alkyl” is preferably an unbranched or branched hydrocarbon radical having 1 to 6 carbon atoms, for example the methyl, ethyl, propyl, isopropyl, 1-butyl, 2-butyl, 2-methylpropyl, tert-butyl, pentyl, 2-methylbutyl, 1,1-dimethylpropyl or hexyl radical;
the term “alkyl” is also preferably a (C
3-
8
)-cycloalkyl group, for example the cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl group;
the term “haloalkyl” is preferably an alkyl group mentioned under the term “(C
1
-C
6
)-alkyl”, in which one or more hydrogen atoms are replaced by the abovementioned halogen atoms, preferably by chlorine or fluorine, for example the trifluoromethyl group, the 1-fluoroethyl group, the 2,2,2-trifluoroethyl group, the chloromethyl, fluoromethyl group, the difluoromethyl group or the 1,1,2,2-tetrafluoroethyl group;
the term “haloalkyl” is also preferably (C
3
-
8
)-halocycloalkyl, i.e. one of the (C
3-
8
)-cycloalkyl radicals listed above in which one or more, in the case of fluorine optionally also all, hydrogen atoms are replaced by halogen, preferably by fluorine or chlorine, for example the 2,2-difluoro- or 2,2-dichlorocyclopropane group or the fluorocyclopentane radical;
the term “alkenyl” is preferably (C
2
-C
6
)-alkenyl, for example the vinyl, allyl, 2-methyl-2-propenyl or 2-butenyl group;
the term “haloalkenyl” is preferably a (C
2
-C
6
)-alkenyl group in which the hydrogen atoms are partially or in the case of fluorine also fully replaced by halogen, preferably by fluorine or chlorine;
the term “alkynyl” is preferably C
2
-C
6
-alkynyl, for example the ethynyl, propargyl, 2-methyl-2-propynyl, 2-butynyl-, 1-pentynyl, 2-pentynyl-, 3-pentynyl- or 4-pentynyl group;
the term “haloalkynyl” is preferably a (C
2
-C
6
)-alkynyl group in which the hydrogen atoms are partially, in the case of fluorine also fully, replaced by halogen atoms, pre

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