Method for producing anellated triazoles and new anellated...

Details Method for producing anellated triazoles and new anellated... Method for producing anellated triazoles and new anellated...

2000-12-18

2003-02-25

Shah, Mukund J. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S223000, C504S228000, C544S010000, C544S064000, C544S184000, C564S036000

Reexamination Certificate

active

06525000

ABSTRACT:

The present invention relates to a process for preparing fused triazoles of the formula I
where:
X—X is C—O, C—S, C—SO, C—CO
2
or C—NR
1
;
V is C═W
2
, R
1
R
2
C—C(═W
2
)— or C(═W
2
)—C(═W
2
);
W
1
, W
2
are oxygen or sulfur;
R
A
is hydrogen, hydroxyl, COOH, COOR
2
, halogen, cyano, C(O)NR
11
R
12
, OR
3
, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, COR
3
, S(O)
n
R
3
or C(O)SR
2
;
R
1
is hydrogen, hydroxyl, halogen, CN, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, COR
3
, CHO, OR
3
, COOR
2
, C(O)SR
2
, C(O)NR
11
R
12
;
R
2
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
2
-C
6
-alkenyl or C
2
-C
6
-alkynyl;
R
3
is C
1
-C
6
-alkyl, C
3
-C
6
-cycloalkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl, carboxyl-C
1
-C
6
-alkyl, C
1
-C
6
-alkoxycarbonyl-C
1
-C
6
-alkyl, C
1
-C
6
-alkylthio-C
1
-C
6
-alkyl, C
1
-C
6
-alkylsulfinyl-C
1
-C
6
-alkyl, C
1
-C
6
-alkylsulfonyl-C
1
-C
6
-alkyl, C
3
-C
6
-cycloalkyl-C
1
-C
6
-alkyl, C
3
-C
6
-alkenyloxycarbonyl-C
1
-C
6
-alkyl, C
3
-C
6
-alkynyloxycarbonyl-C
1
-C
6
-alkyl, C
3
-C
6
-cycloalkoxy-C
1
-C
6
-alkyl, C
3
-C
6
-alkenyloxy-C
1
-C
6
-alkyl, C
3
-C
6
-alkynyloxy-C
1
-C
6
-alkyl, C
1
-C
6
-haloalkoxy-C
1
-C
6
-alkyl, C
3
-C
6
-haloalkenyloxy-C
1
-C
6
-alkyl, C
3
-C
6
-haloalkynyloxy-C
1
-C
6
-alkyl, C
3
-C
6
-cycloalkyl-C
1
-C
6
-thioalkyl, C
3
-C
6
-alkenylthio-C
1
-C
6
-alkyl, C
3
-C
6
-alkynylthio-C
1
-C
6
-alkyl, cyano-C
1
-C
6
-alkyl, C
3
-C
6
-halocyclo-C
1
-C
6
-alkyl, halo-C
3
-C
6
-alkenyl, C
1
-C
6
-alkoxy-C
3
-C
6
-alkenyl, C
1
-C
6
-haloalkoxy-C
3
-C
6
-alkenyl, C
1
-C
6
-alkylthio-C
3
-C
6
-alkenyl, C
3
-C
6
-haloalkynyl, C
1
-C
6
-alkoxy-C
3
-C
6
-alkynyl, C
3
-C
6
-haloalkoxyalkynyl, C
1
-C
6
-alkylthioalkynyl, C
1
-C
6
-alkylcarbonyl, CHR
16
COR
17
, CHR
16
P(O) (OR
17
)
2
, P(O) (OR
17
)
2
, CHR
16
P(S) (OR
17
)
2
, CHR
16
C(O)NR
11
R
12
, CHR
16
C(O)NH
2
, C
1
-C
6
-alkyl, which is substituted by phenoxy or benzyloxy, where the rings for their part may be substituted by halogen, C
1
-C
4
-alkyl or C
1
-C
4
-haloalkyl, benzyl which may be substituted by halogen, C
1
-C
4
-alkyl or C
1
-C
4
-haloalkyl, or is phenyl or pyridyl which may be substituted by halogen, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl or C
1
-C
4
-alkoxy;
m has the value 0, 1, 2 or 3;
n has the value 0, 1 or 2;
Q is one of the radicals Q-1 to Q-7
 where
Y
2
is oxygen or sulfur;
R
4
is hydrogen or halogen;
R
5
is C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, OCH
3
, OCHF
2
, halogen, CN or NO
2
;
R
6
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
haloalkyl, halogen, OR
10
, S(O)
n
R
10
, COR
10
, COOR
10
, C(O)SR
10
, SCH
2
C≡CH, C(O)NR
11
R
12
, CHO, CH═CHCC—OR
10
, CO—ON═CR
13
R
14
, NO
2
, CN, NHCO
2
R
15
, NHSO
2
NHR
15
, —C(R
18
)═C(R
19
)—CO—R
20
, —CH(R
18
)—CH(R
19
)—CO—R
20
, —C(R
18)═C(R
19
)—CO—N(R
20
, R
21
), —CH(R
18
)—CH(R
19
)—CO—N(R
20
, R
21
), —C(R
21
)═N—OR
22
, —COOC(R
23
)(R
24
)—COOR
25
, —CO—N(R
26
)—OR
22
or —C(OR
27
)═N—OR
22
;
R
7
, R
8
independently of one another are hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl or halogen; if Q is Q-2, Q-5 or Q-6, R
7
and R
8
may, together with the linking carbon atom, form a group C═O;
R
9
is C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl or C
2
-C
6
-alkynyl;
R
10
is one of the radicals indicated under R
3
;
R
11
, R
13
independently of one another are hydrogen or C
1
-C
6
-alkyl;
R
12
, R
14
independently of one another are C
1
-C
6
-alkyl or phenyl which may be substituted by halogen, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl or C
1
-C
4
-alkoxy;
R
11
, and R
12
together may be a group —(CH
2
)
5
—, —(CH
2
)
4
— or —CH
2
CH
2
OCH
2
CH
2
— where each ring may be substituted by C
1
-C
3
-alkyl, or may be phenyl or benzyl;
R
13
and R
14
together with the linking carbon atom may also form a C
3
-C
8
-cycloalkyl group;
R
15
is C
1
-C
6
-alkyl or C
1
-C
6
-haloalkyl;
R
16
is hydrogen or C
1
-C
6
-alkyl;
R
17
is C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl or C
2
-C
6
-alkynyl;
R
18
, R
23
, R
24
are each hydrogen or C
1
-C
3
-alkyl;
R
19
is halogen, cyano or methyl;
R
20
is hydroxyl, C
1
-C
6
-alkoxy, C
3
-C
6
-cycloalkoxy, C
1
-C
4
-alkoxy-C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio-C
1
-C
4
-alkoxy, C
1
-C
4
-alkylsulfinyl-C
1
-C
4
-alkoxy, C
1
-C
4
-alkylsulfonyl-C
1
-C
4
-alkoxy, cyano-C
1
-C
6
-alkoxy, C
1
-C
4
-alkoxycarbonyl-C
1
-C
4
-alkoxy, C
3
-C
6
-alkenyloxy, C
3
-C
6
-alkynyloxy, partially or fully halogenated C
1
-C
6
-alkoxy, partially or fully halogenated C
3
-C
6
-alkenyloxy, partially or fully halogenated C
3
-C
6
-alkynyloxy, C
1
-C
6
-alkylthio, furthermore C
1
-C
6
-alkoxy which may carry two additional C
1
-C
6
-alkoxy substituents,
R
21
is hydrogen, C
1
-C
6
-alkyl or C
1
-C
6
-haloalkyl;
R
22
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
4
-alkoxy-C
1
-C
4
-alkyl, C
1
-C
6
-haloalkyl, C
1
C
6
-cyanoalkyl, C
3
-C
6
-cycloalkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, C
3
-C
6
-haloalkenyl, C
3
-C
6
-haloalkynyl, carboxyl-C
1
-C
6
-alkyl, C
1
-C
6
-alkoxycarbonyl-C
1
-C
4
-alkyl, C
1
-C
6
-alkylcarbonyl-C
1
-C
6
-alkyl or C
1
-C
6
-alkylcarbonyloxy-C
1
-C
6
-alkyl;
R
25
is hydrogen, C
1
-C
6
-alkyl, C
3
-C
6
-cycloalkyl, C
1
-C
6
-alkoxy-C
1
-C
4
-alkyl, cyano-C
1
-C
6
-alkyl, halo-C
1
-C
6
-alkyl, C
3
-C
6
-alkenyl or C
3
-C
6
-alkynyl;
R
26
, R
27
independently of one another are C
1
-C
6
-alkyl, C
1
-C
4
-alkoxy-C
1
-C
4
-alkyl, C
3
-C
6
-cycloalkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-cyanoalkyl, C
3
-C
6
-haloalkenyl, C
3
-C
6
-haloalkynyl or C
1
-C
6
-alkoxycarbonyl-C
1
-C
4
-alkyl;
R
26
is additionally hydrogen.
Additionally, the invention relates to novel fused triazoles of the formula I′
where Z is oxygen, sulfur, SO or SO
2
, to their use in crop protection, and to fuse triazoles of the formula I″.
Furthermore, the invention relates to substituted N-methyleneimino-N′-phenylureas of the formula III′,
where:
Z is O, S, S═O or SO
2
;
R
A
is halogen or C
1
-C
3
-alkyl;
W
1
is oxygen or sulfur;
R
4
is hydrogen or halogen;
R
5
is halogen, cyano or trifluoromethyl;
R
6
is a group —C(R
18
)═C(R
19
)—CO—R
20
, —CH(R
18
)—CH(R
19
)—CO—R
20
, —C(R
18
)═C(R
19
)—CO—N(R
20
,R
21
) —CH(R
18
)—CH(R
19
)—CO—N—(R
20
, R
21
), —C(R
21
)═N—OR
22
, —CO—OC(R
23
)(R
24
)—CO—OR
25
, CO—N(R
26
)—OR
22
or —C(OR
27
)═N—OR
22
;
R
18
, R
23
,
R
24
are each hydrogen or C
1
-C
3
-alkyl;
R
19
is halogen, cyano or methyl;
R
20
is hydroxyl, C
1
-C
6
-alkoxy, C
3
-C
6
-cycloalkoxy, C
1
-C
4
-alkoxy-C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio-C
1
-C
4
-alkoxy, C
1
-C
4
-alkylsulfinyl-C
1
-C
4
-alkoxy, C
1
-C
4
-alkylsulfonyl-C
1
-C
4
-alkoxy, cyano-C
1
-C
6
-alkoxy, C
1
-C
4
-alkoxycarbonyl-C
1
-C
4
-alkoxy, C
3
-C
6
-alkenyloxy, C
3
-C
6
-alkynyloxy, partially or fully halogenated C
1
-C
6
-alkoxy, partially or fully halogenated C
3
-C
6
-alkenyloxy, partially or fully halogenated C
3
-C
6
-alkynyloxy, C
1
-C
6
-alkylthio, furthermore C
1
-C
6
-alkoxy which may carry two additional C
1
-C
6
-alkoxy substituents;
R
21
is hydrogen, C
1
-C
6
-alkyl or C
1
-C
6
-haloalkyl;
R
22
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
4
-alkoxy-C
1
-C
4
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-cyanoalkyl, C
3
-C
6
-cycloalkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, C
3
-C
6
-haloalkenyl, C
3
-C
6
-haloalkynyl, carboxyl-C
1
-C
6
-alkyl, C
1
-C
6
-alkoxycarbonyl-C
1
-C
4
-alkyl, C
1
-C
6
-alkylcarbonyl-C
1
-C
6
-alkyl or C
1
-C
6
-alkylcarbonyloxy-C
1
-C
6
-alkyl;
R
25
is hydrogen, C
1
-C
6
-alkyl, C
3
-C
6
-cycloalkyl, C
1
-C
6
-alkoxy-C
1
-C
4
-alkyl, cyano-C
1
-C
6
-alkyl, halo-C
1
-C
6
-alkyl, C
3
-C
6
-alkenyl or C
3
-C
6
-alkynyl;
R
26
, R
27
are C
1
-C
6
-alkyl, C
1
-C
4
-alkoxy-C
1
-C
4
-alkyl, C
3
-C
6
-cycloalkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-cyanoalkyl, C
3
-C
6
-haloalkenyl, C
3
-C
6
-haloalkynyl or C
1
-C
6
-alkoxycarbonyl-C
1
-C
4
-alkyl, and
R
26
is additio

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