Plant protecting and regulating compositions – Plant growth regulating compositions – Plural active ingredients
Reexamination Certificate
2002-01-17
2003-02-18
Clardy, S. Mark (Department: 1616)
Plant protecting and regulating compositions
Plant growth regulating compositions
Plural active ingredients
C504S138000
Reexamination Certificate
active
06521567
ABSTRACT:
TECHNICAL FIELD
The present invention relates to a new herbicidal composition.
BACKGROUND ART
At the present time, it is known that an N-phenyltetrahydrophthalimide compound represented by Chemical Formula (1) described below has herbicidal activity (See U.S. Pat. No. 4,770,695, U.S. Pat. No. 4,640,707, U.S. Pat. No. 5,062,884 and so on).
In a field of herbicide, requested are how can an application of less amount of herbicide attain same herbicidal effect as an application of usual amount of it.
DISCLOSURE OF INVENTION
The present inventor has intensively studied to find out a method for boosting herbicidal activity of the N-phenyltetrahydrophthalimide compound. As a result he has found that, when the N-phenyltetrahydrophthalimide compound was applied with an insecticidal organophosphorus compound, the herbicidal activity of the N-phenyltetrahydrophthalimide compound against weeds was higher than when the N-phenyltetrahydrophthalimide compound was solely applied.
Thus, the present invention provides a herbicidal composition of the N-phenyltetrahydrophthalimide compound represented by Chemical Formula (1):
wherein R
1
represents hydrogen or halogen; R
2
represents halogen and R
3
represents hydrogen, (C1-C8 alkoxy)carbonyl C1-C2 alkoxy, C1-C6 alkynyloxy or (C1-C8 alkoxy)carbonyl C2-C3 haloalkenyl, or R
2
and R
3
represent together —O—CHR
4
—C(═O)—NR
5
—, whose oxygen connected to 4-position of the benzene ring, whose nitrogen connected to 5-position of the benzene ring, wherein R
4
represents hydrogen or methyl and R
5
represents C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl or (C1-C3 alkoxy) C1-C3 alkyl,
and an effective amount for increasing herbicidal activity of the N-phenyltetrahydrophthalimide compound of an insecticidal organophosphorus compound (hereinafter, referred to as the present composition); and a method for controlling weeds which comprises of applying said N-phenyltetrahydrophthalimide compound with the insecticidal organophosphorus compound to weeds or to a place where weeds are growing or will grow (hereinafter referred to as the present method).
The N-phenyltetrahydrophthalimide compound represented by Chemical Formula (1) (hereinafter referred to as the present imide compound) includes the compounds described below.
A compound wherein R
2
and R
3
are together —O—CHR
4
—C(═O)—NR
5
— in Chemical Formula (1), that is represented by Chemical Formula (4):
wherein R
1
, R
4
and R
5
are as defined above;
a compound wherein R
1
is fluorine in Chemical Formula (4);
a compound wherein R
4
is hydrogen in Chemical Formula (4);
a compound wherein R
5
is C3-C6 alkynyl in Chemical Formula (4);
a compound wherein R
1
is fluorine, R
4
is hydrogen and R
5
is C3-C6 alkynyl in Chemical Formula (4);
a compound wherein R
2
is R
21
and R
3
is R
31
in the Chemical Formula (1), that is represented by Chemical Formula (5):
wherein R
1
are as defined above, R
21
represents halogen and R
31
represents hydrogen, (C1-C8 alkoxy)carbonyl C1-C2 alkoxy, C1-C6 alkynyloxy or (C1-C8 alkoxy)carbonyl C2-C3 haloalkenyl;
a compound wherein R
1
is fluorine in Chemical Formula (5);
a compound wherein R
21
is chlorine in Chemical Formula (5);
a compound wherein R
31
is (C1-C8 alkoxy)carbonyl C1-C2 alkoxy in Chemical Formula (5);
a compound wherein R
31
is C1-C6 alkynyloxy in Chemical Formula (5);
a compound wherein R
31
is (C1-C8 alkoxy)carbonyl C2-C3 haloalkenyl in Chemical Formula (5);
a compound wherein R
1
is fluorine, R
21
is chlorine and R
31
is (C1-C8 alkoxy)carbonyl C1-C2 alkoxy in Chemical Formula (5).
Furthermore, the present imide compound includes the compounds described below.
N-(7-fluoro-3,4-dihydro-3-oxo-4-prop-2-ynyl-2H-1,4-benzoxazin-6-yl)cyclohex-1-ene-1,2-dicarboxamide
(common name: flumioxazin);
pentyl[2-chloro-5-(cyclohex-1-ene-1,2-dicarboximido)-4-fluorophenoxy]acetate
(common name: flumiclorac-pentyl);
(Z)-ethyl 2-chloro-3-[2-chloro-5-(cyclohex-1-ene-1,2-dicarboximido)phenyl]acrylate
(common name: cinidon-ethyl);
N-(4-chlorophenyl)cyclohex-1-ene-1,2-dicarboxamide
(common name: chlorphthalim).
The insecticidal organophosphorus compound in the present invention includes, for example, the compounds described below.
A compound represented by Chemical Fonnula (6):
wherein X
1
represents oxygen or sulfur, X
2
represents oxygen, sulfur or direct bond between phosphorous atom and R
8
, R
6
represents lower alkyl, R
7
represents lower alkoxy, lower alkylthio, lower alkylcarbonylamino or phenyl, R
8
represents optionally substituted alkyl, optionally substituted alkenyl, optionally substituted phenyl or optionally substituted heteroaryl;
a compound wherein X
1
is sulfur, X
2
is oxygen, R
6
is C1-C4 alkyl, R
7
is C1-C4 alkylcarbonylamino and R
8
is optionally substituted C1-C4 alkyl in the Chemical Formula (6);
a compound wherein X
1
is sulfur, X
2
is sulfur, R
6
is C1-C4 alkyl, R
7
is C1-C4 alkoxy and R
8
is optionally substituted C1-C4 alkyl in the Chemical Formula (6);
a compound wherein X
1
is sulfur, X
2
is oxygen, R
6
is C1-C4 alkyl, R
7
is C1-C4 alkoxy and R
8
is optionally substituted alkenyl in the Chemical Formula (6);
a compound wherein X
1
is sulfur, X
2
is oxygen, R
6
is C1-C4 alkyl, R
7
is C1-C4 alkoxy and R
8
is optionally substituted phenyl in the Chemical Formula (6);
a compound wherein X
1
is sulfur, X
2
is oxygen, R
6
is C1-C4 alkyl, R
7
is C1-C4 alkylthio and R
8
is optionally substituted phenyl in the Chemical Formula (6);
a compound wherein X
1
is sulfur, X
2
is oxygen, R
6
is C1-C4 alkyl, R
7
is C1-C4 alkoxy and R
8
is optionally substituted pyrimidinyl in the Chemical Formula (6);
a compound wherein X
1
is sulfur, X
2
is oxygen, R
6
is C1-C4 alkyl, R
7
is C1-C4 alkoxy and R
8
is optionally substituted pyridyl in the Chemical Formula (6);
a compound wherein X
1
is sulfur, X2 is oxygen, R
6
is C1-C4 alkyl, R
7
is C1-C4 alkoxy and R
8
is optionally substituted isoxazolyl in the Chemical Formula (6).
Furthermore, the insecticidal organophosphorus compound includes the compounds described below.
O,O-dimethyl O-4-nitro-m-tolyl phosphorothioate (common name: fenitrothion);
O,O-dimethyl O-4-methylthio-m-tolyl phosphorothioate (common name: fenthion);
O,O-diethyl O-2-isopropyl-6-methylpyrimidin-4-yl phosphorothioate (common name: diazinon);
O,O-diethyl O-3,5,6-trichloro-2-pyridyl phosphorothioate (common name: chlorpyrifos);
O,S-dimethyl acetylphosphoramidothioate (common name: acephate);
S-2,3-dihydro-5-methoxy-2-oxo-1,3,4-thiadiazol-3-ylmethyl O,O-dimethyl phosphorodithioate (common name: methidathion);
O,O-diethyl S-2-ethylthioethyl phosphorodithioate (common name: disulfoton);
2,2-dichlorovinyl dimethyl phosphate (common name: dichlorvos);
O-ethyl O-4-(methylthio)phenyl S-propyl phosphorodithioate (common name: sulprofos);
O-4-cyanophenyl O,O-dimethyl phosphorothioate (common name: cyanophos);
O,O-dimethyl S-methylcarbamoylmethyl phosphorodithioate (common name: dimethoate);
S-&agr;-ethoxycarbamoylbenzyl O,O-dimethyl phosphorodithioate (common name: phenthoate);
diethyl (dimethoxythiophosphorylthio)succinate (common name: malathion);
dimethyl 2,2,2-trichloro-1-hydroxyethylphosphonate (common name: trichlorfon);
S-(3,4-dihydro-4-oxobenzo[d]-[1,2,3]-triazin-3-ylmethyl) O,O-dimethyl phosphorodithioate (common name: azinphos-methyl);
dimethyl (E)-1-methyl-2-(methylcarbamoyl)vinyl phosphate (common name: monocrotophos);
O,O,O′,O′-tetraethyl S,S′-methylene bis(phosphorodithioate) (common name: ethion);
S-2-ethylthioethyl O,O-dimethyl phosphorodithioate (common name: thiometon);
O,O-diethyl O-(5-phenyl-1,2-oxazol-3-yl) phosphorothioate (common name: isoxathion);
O,O-dimethyl S-2-(1-methylcarbamoylethylthio)ethyl phosphorothioate (common name: vamidothion);
O-2,4-dichlorophenyl O-ethyl S-propyl phosphorodithioate (common name: prothiofos);
S-2-ethylsulfinyl-1-methylethyl] O,O-dimethyl phosphorothioate (common name: xydeprofos).
The present imide compound can be produced according to the procedures described, for example,
Clardy S. Mark
Sumitomo Chemical Company Limited
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