JPS5849345A - Novel phenoxyphenylamino acid derivative, manufacture and herbicide and composition containing same - Google Patents

Abstract

(57) [Abstract] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a process for producing a tr rough phenoxy phenyl amino acid derivative, a composition containing the novel compound, and the use of the compound for controlling undesirable plant growth or for controlling cotton and potato plants. Diphenyl ethers with herbicidal properties are described in European Patent Application No. 27.555, U.S. Pat.
specification and West German Publication No. 2,311,638
I know the issue. Historically, phenoxyphenylthioalkane carbon eIk derivatives having herbicidal properties 1 have been described in European Patent Application No. 351. The novel compounds of the present invention have the following formula I: 1 [wherein X is Represents a hydrogen atom, a chlorine atom - one fluorine atom, or a bromine atom; R1 is a hydrogen atom, a nitrone group, an alkyl group having 1 to 4 carbon atoms, a fluorine group having 2 to 4 carbon atoms, or a fluorine atom having 1 to 4 carbon atoms; 4 alkylcarbonyl group or C2-C4 alkenylcarbonyl group which is unsubstituted or has tits with one or more halogen atoms.

Q is the following formula:
The adjacent substituents A, E', t;', L- and M' represent open bonds between the two carbon atoms to which they are attached; A, E, G, L and M are water; 31
one or two of the atoms or A, E, G, L and M are also 1〇R2;
, , -8R'' or -〇〇OR'
, R4, R6, Rh and R7 represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; a, b
, c and d represent 0 or IV'; or R1 and G together represent a trimethylene bridge and a,
b, c and d represent 0) carbon atom number 1
1 to 5 straight or branched aliphatic radicals. ;so), teZ is s, 4: -COOθMψ, -coo♂,
-CO8R'.

-co to R'RI0. -CUR” or -CN, (
In the formula, M♀ is the same cation *R'' is a water 1g atom; - a C1-C8 alkyl group unsubstituted or substituted by a rogen atom, cyano or a C1-C4 alkoxy group; carbon alkenyl having 2 to 8 atoms; or an alkynyl group having 3 to 8 carbon atoms; R9 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a cycloalkyl group having 5 to 6 carbon atoms;
RIO&'! Hydrogen atom; Amino group: Hydroxyl group: A C1-C4 alkyl group substituted or substituted with a C1-C4 alkoxy group, or a C2-C4 flukynyl group, carbon a 1 to 4σ alkoxy group; or a cycloalkylaminocarbonyl group having 3 to 6 carbon atoms;
is a bulky atom of water: or 1% of carbon atoms unsubstituted or substituted with an alkoxy group having 1 to 4 carbon atoms, L.
However, in the compound, K R1 is a water bulk atom and a, b, ・C and d are 0 and f! (1) G is -OR"; -CO
OR';4 L <42-OR', -8R' 4
L <12-CUOR? -t"f is a substituted alkyl group having 1 to 4 carbon atoms, or (ii) Gj+5 and α both represent an alkyl group having 1 to 4 carbon atoms.]

C1-C4delkyl, either by itself or as part of another group, can be represented by methyl, ethyl, n-propyl, improbi, n-butyl, 2-
butyl, tert-butyl and isobutyl, and C1-C4alkoxy is methoxy,
These are ethoxy, n-propoxy, inpropoxy, n-butoxy, 2-butoxy, Hg5-butoxy and isobutoxy groups. The alkyl group having 1 to 8 carbon atoms includes the alkyl groups listed under '' above, n-pentyl, n-hexyl, n-hebutyl, n-octyl and isomers thereof.

Alkenyl groups and alkynyl groups, either by themselves or as part of other substituents, include straight-chain and branched groups corresponding to the representation of the number of carbon atoms.

Cycloalkyl having 5 to 6 carbon atoms represents cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

Suitable cation ends are preferably ammonium cations, Kanasu cations, organic nitrogen bases, sulfonium cations or sulfoxonium cations.

Suitable metals for salt formation are alkaline earth metals such as magnesium or calcium and alkali metals such as lithium, potassium, preferably sodium. Made of synthetic fiber,
Examples include iron, nickel, cobalt, copper, zinc, chromium, and magnesium. Examples of suitable organic nitrogen bases for salt formation include primary, secondary and 5fJ aliphatic and aromatic abans, which may be hydroxylated in their hydrocarbon groups, e.g. Methylamine, ethylamine, n-propylamine, inglovirine, four isomers of butylamine, dimethylamine, diethylamine, di-n-propylamine, diisopropylamine,
Di-n-7 teramine, pyrrolidine, piperidine, morpholine, trimethylamine, triethylamine, tri-n-propylamine, quinuclidine, pyridine, quinolidine, isoquinoline, as well as ethanolamine, globanolamine, jetanolamine, and Ethanolamine, also a tetraalkylammonium whose alkyl moieties are independently linear or branched C1 -C4, such as tetraethelammonium, tetraethelammonium or trimethyl Ammonium also includes quaternary ammonium hydroxides such as trimeterpendylammonium, triethylbenzylammonium and trimethyl-2-hydroxyethylammonium.

With respect to sulfonium and sulfoxonium cations, we mean -0SH8 and -"5IO)Hs, in which one or more hydrogen atoms can also be replaced by an organic radical, e.g. These are the hydrocarbon radicals listed in .

A @spring or branched C1-C5 aliphatic radical as Q is taken to mean acyclic hydrocarbon radicals, which are saturated or have olefinic unsaturation. , while the indicated number of IR atoms is Il conversion iA, E, G, L, M,
A', ECGzI15YohiM' includes only non-v1 substituted or substituted alkyl radicals.

When R1 and G together form a trimethylene bridge, a pyrrolidino ring is present.

formula! Preferred compounds include one of the following compound groups:
belongs to.

tal In the formula ■, X represents a hydrogen atom, a chlorine atom, a fluorine atom, or a bromine atom, and R1 is a hydrogen atom,
a nitrone group, a C1-C4 alkyl group, or a C1-C4 alkylcarbonyl group unsubstituted or substituted with a halogen atom of 11 VA or more, Q represents the following formula: (wherein A- E', G', L' and M are hydrogen atoms or alkyl groups having 1 to 4 R atoms, or 291
7) Adjacent substituents A', Bi, GL' and M' are bonds between the two #i2 atoms to which they are bonded. A, E, G, LjI5 and M are water ILFj
7A child or A, E, G, L and M') 1 @4
h L < fj 2 @Ka1terOR” ;-8R”
;-CO(JR'; carbon atom l1l11 (-4 alkyl group; or -OR', -8R' or 4
2-COOR7 is substituted with FL't-alkyl group having 1 to 4 vertical atoms (R", R", R', R',
R8, Oyor) R'kl represents an alkyl group with 1 or less carbon atoms (, 4); a, b, c and d represent 0 or 1; or R1 and G are the same represents a trimethylene bridge, and a, b, c and d represent 0; (d) represents a linear or branched aliphatic radical having 1 to 5 vertical atoms;
°M! , -COOR'', -CONtrr' or -
CN (in the formula, M♀ represents a cation or a hydrogen atom; an alkyl group having 1 to 4 carbon atoms that is non-am or till substituted by a halogen atom or an alkoxy group having 1 to 4 carbon atoms; 2 to 4 alkenyl group, R'' is a water atom; an alkyl group with t11 to 4 atoms; or a cycloalkyl group having 5 to 6 carbon atoms; RLO is a hydrogen atom; an amino group; a hydroxyl group; a carbon an alkyl group having 1 to 4 vertical atoms, unsubstituted or substituted by an alkoxy group having 1 to 4 atoms; or an alkenyl group having 2 to 4 carbon atoms, 1 vertical atom;
to 4 alkoxy groups; or cycloalkylaminocarbonyl groups having 3 to 6 vertical atoms), provided that in the compound, KRI is set by a water bulk atom and a, b, c and when d is 00, +II Q is -C
OOR'; 4 L <Bar0R--8R' is also C0OR' Alkyl group having 1 to 4 vertical atoms substituted by K, or [lil G and G' both have 1 to 4 carbon atoms A compound that is an alkyl group.

In the formula ■, 4 is a hydrogen atom and a chlorine atom.

represents a fluorine atom or a bromine atom, 1 represents a water bulk atom or an alkyl group having 1 to 4 carbon atoms, and Q represents the following formula: (wherein A, E, G, L and MFi hydrogen atoms also represent A, E , one or two of G, L and M are also 10";-sR";-cooh'; carbon atom number 1
to 4 alkyl groups: or -014,', -8R'
or carbon atom a 1 substituted by -coon'
NaiL, 4 (D 7 Ru* Ru group (B″, m”
, R', kL", kim" and °W represent a hydrogen atom or a C1-C4 alkyl group; a, b, c and d represent 0 or #-t1; or) tl and G together represent a trimethylene bridge, and a, b, c and d represent 0), a linear or branched alkylene radical having 1 to 5 vertical atoms; Z is -cooeJ, -COOR; ” ,
-CONk4r''R''・,-COR'l or -CN C In the formula, ``a'' represents a metal cation, b- represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and W and R'' represent a hydrogen atom or R1'' is an alkyl group having 1 to 4 carbon atoms;
9 represents an alkyl group having 1 to 4 carbon atoms substituted by an oxy group, with the proviso that in the compounds;

At the same time, R1 is a hydrogen atom and a, b, C and d are 0
When , G is -oR';-coo14'; also L
<H-OR', -1'4 L<H-COOR'Kj 9
Compounds which are 11-substituted C1 -C4 alkyl groups.

(C) In formula I, s is a hydrogen atom or a chlorine atom.

Represents a fluorine atom or a bromine atom, R'' is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and Q is the following formula: (In the formula, A, E, G, L and M are hydrogen atoms Honshiguke A, g, G, L and M 1-14 are also-
0)L'';-814'';-COOR'; C1-C4 alkyl group; or -〇R', -8
174 alkyl group with 1 anti-atom substituted by R' or -COOR' (R1, rule', R'
, R'' and 7 represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; two of the symbols a, b, c and d are 0, and the other two represent 0 or 1; Shiku-a R1 and G together represent a trimethylene bridge,
and a, b, c, and d represent 0), a straight chain having 1 to 5 carbon atoms, or -CN (wherein, a, b, c, and d represent 0)
, R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and R 11 represents an alkyl group having 1 to 4 carbon atoms substituted with an alkoxy group having 1 to 4 carbon atoms), However, when 1 is a hydrogen atom and a, b, c and d are O in the compound, G
is -OP; -COOl4; or -OR', -8
R” or carbon 1 substituted with -cooa'
A compound that is an alkyl group having 9 molecules from 1 to 4.

(d) In formula I, X represents a hydrogen atom or a chlorine atom, and R'' is a hydrogen atom, a nitroso group, a methyl group,
Methylcarbonyl group, ethylcarbonyl group, vinylcarbonyl group, chloromethylcarbonyl group, trichloromethylcarbonyl group or trifluoromethylcarbonyl group; M' is a hydrogen atom or a C1-C4 alkyl group, or two adjacent substituents A', E', G',
L' and M' represent the bonds between the 2 carbon atoms to which they are bonded; A, g, G, L and M are also hydrogen atoms; one of A, E, G, L and M; Cut
&-01-L", -8R--COOR'; an alkyl group having 1 to 4 carbon atoms; or -OR'.

C1-C4 alkyl group substituted by -8R' or -coon'< B*, kcl,
m4゜ms, R@ and ni&? represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; a.

b, c and d represent 0 or 1; or kL
I and G together represent trimethylene, and a,
b, 1 carbon atom (c and d represent the mouth)
to 5 linear or branched chains or an aliphatic radical, where Z is -COO0, '' is a cation, and 'R' is a hydrogen atom: a gen atom or a carbon atom number of 1 to 4
an alkyl group having 1 to 8 carbon atoms unsubstituted or substituted with an alkoxy group; a carbon atom hydrogen atom; an alkyl group having 1 to 4 carbon atoms; or a cycloalkyl group having 3 to 6 carbon atoms; , 'R' is a hydrogen atom; an amino group; a hydroxyl group; a carbon atom which is unsubstituted or substituted with an alkoxy group having 1 to 4 carbon atoms;
an alkyl group having 2 to 4 carbon atoms; an alkynyl group having 2 to 4 carbon atoms; an alkoxy group having 1 to 4 carbon atoms; or a cycloalkylaminocarbonyl group having 3 to 6 carbon atoms). , 9, and in the compound, at the same time, 1 is water, an elementary atom, and a, b, c, and d are 0, (:)G-COOl4; or
1l-OR'e'-8B-" 41. < Fi-C
OOkL7K yo9 Substituted carbon atom number 4
(1) A compound in which G and G' are both alkyl groups having 1 to 4 carbon atoms.

(e) In formula I, X is a hydrogen atom or a chlorine atom, 1 is a hydrogen atom or a methyl group, Q is the following formula: In the formula 1, A, E, G, L and M are hydrogen atoms or One of g, G, L and M is also one OR'; -
8R1neeCOO几4: C1-C4 alkyl group; or -〇R'', -8R@ or -c
Number of carbon atoms substituted by ookL' 1 ft il,
4 tD 7 L* A/ group (kL', R',
R', R', R' and V represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; symbol a,
Two of b, c and d are 0, the other two are 0 or 1
or R1 and q together represent a trimethylene bridge and a, b, c and d represent 0), a 1,5 straight-chain or branched alkylene radical having 1 carbon atom; Z is 1000'M''), -c
oo direct -col 11 or -CN (wherein, H is substituted with a metal cation, R1 is a hydrogen atom or a C1-C4 alkyl group, and R11 is substituted with a C1-C4 alkoxy group) (represents an alkyl group having 1 to 4 carbon atoms), provided that in the compound, when R1 is a hydrogen atom and a, b, c and d are 0, G is -014,': CUOR '; 4 L
<ti-0ft', -8B'' 4. A compound in which L< is an alkyl group having 1 to 4 carbon atoms substituted with -COO.

(D In formula (2), X represents a hydrogen atom or a chlorine atom, and W represents a hydrogen atom, a nitron base, or an alkyl group having 1 to 4 carbon atoms.

an alkenyl group having 2 to 4 carbon atoms, an alkylcarbonyl group having 1 to 4 carbon atoms, or an alkenylcarbonyl group having 2 to 4 carbon atoms, unsubstituted or substituted with F'i 1 to 3 chlorine or fluorine atoms; and Q is 1,5-pentamethylene/ or the following formula: (where AI, El, Gg, L H and M' are hydrogen atoms or λr, Er, Gr, L z and M' one of which is also a C1 -C4 alkyl group or two adjacent substituents A', E', Q',
L' and M' represent the bonds between the two carbon atoms to which they are attached; A, E, G, L and M are hydrogen atoms or one of AsE, G, t and M is also a carboxyl group. ; C1-C4 alkoxycarbonyl group; represents a C1-C4 alkyl group unsubstituted or monosubstituted by a hydroxyl group or a C1-C4 alkylthio group, and the symbol a? bIC
and two of d are 0 and the other two represent 0 or 1; or 8m and G together represent a trimethylene bridge and a, b, c and d represent O) having 1 to 1 carbon atoms; 3 represents a straight-chain or branched aliphatic radical, Z is -co<R, -COO, -COO, and -> is -CN (in the formula, 1Me is an alkali metal cation). , 1 is a hydrogen atom; a chlorine atom or a carbon atom of 1 to 4
unsubstituted or monosubstituted g with an alkoxy group of
- is an alkyl group having 1 to 8 atoms; or an alkenyl group having 2 to 8 carbon atoms or an alkynyl group having 3 to 8 carbon atoms;
a cycloalkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms; k'' is a hydrogen atom niamino group; hydroxyl group; 4 alkyl group; or an alkenyl group having 2 to 4 carbon atoms;
(represents an alkoxy group having 1 to 4 carbon atoms or a cycloalkylaminocarbonyl group having 3 to 6 carbon atoms), provided that in the compound, at the same time, approximately 1 is a hydrogen atom and a, b, c and d are When it is 0, (1)
G is a carboxyl group; an alkoxycarbonyl group having 1 to 4 carbon atoms; or a hydroxyl group or an alkyl group having 1 to 4 carbon atoms monosubstituted by a 74 alkylthio group; or (-)G and A compound in which both α's represent an alkyl group having 1 to 4 carbon atoms.

(-In formula I, X is a hydrogen atom, W is a hydrogen atom, Q is 1,2-ethylene, and 2 car CON, -
COOR", -CO8B", -CONR'R"
.

-COB"4 L, < tri -CN (in the formula, ?
! ``!Ukaf1y, kL8 is a hydrogen atom;] ・C1-C8 unsubstituted or substituted with a rogen atom, a cyano group, or a C1-C4 alkoxy group
or an alkenyl group having 2 to 8 carbon atoms; or an alkynyl group having 3 to 8 carbon atoms; 1 is a hydrogen atom; A cycloalkyl group, R'' is a hydrogen atom; an amino group; a hydroxyl group; an alkyl group having 1 to 4 carbon atoms, unsubstituted or substituted with an alkoxy group having 1 to 4 carbon atoms; or a C 2 to 4 alkyl group; 4 alkynyl group, carbon number 1 to 4
an alkogia group or a cycloalaminocarbonyl group having 3 to 6 carbon atoms t, ill is a hydrogen atom; or an alkyl group having 1 to 4 carbon atoms which is unsubstituted or substituted with an alkoxy group having 1 to 4 carbon atoms; A compound that is

(h) In formula I, X is a hydrogen atom or a chlorine atom.

represents a fluorine atom or a bromine atom, and R1 is a hydrogen atom, a nitroso group, an alkyl group having 1 to 4 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, an alkylcarbonyl group having 1 to 4 carbon atoms, or an alkylcarbonyl group having 1 to 4 carbon atoms; 2 to 4 alkenylcarbonyl groups, unsubstituted or substituted with one or more halo, gen atoms, 'Q is 1,5-pentamethylene or ', G', L' and M' are hydrogen atoms or one of A', B', G'', L' and M' still contains a methyl group or two adjacent substituents A', ・h' , G', L'' and M' represent the bonds between the two carbon atoms to which they are attached;
A.J.G.

L and M are hydrogen atoms, specifically A, g, G, L and M
One of o also represents a carboxyl group, a methoxycarbonyl group, an ethoxycarbonyl group, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, or a 2-methylthioethyl group, and the symbol at
Two of bjc and d are mouths, the other two are 0 or 1
represents; or 4d B' and Q back the 1-yrimethylene bridge, and a, b.

C 1 to 3 straight-chain or branched aliphatic radicals (→r→ cal) of which C and d are 0; Z is -COOMe, -COOR@;

-CONIL"lL" 4 L (d -CN (:&
where, J2 u f ) represents a lithium cation, V represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a 2-chlorinated ethyl group, a 2-methoxyethyl group, an allyl group or a prop-2-ynyl group; 9 is a hydrogen atom.

10 is a hydrogen atom, an amino group, a hydroxyl group, an alkyl group having 1 to 3 carbon atoms, a 2-methoxyethyl group, a buty-5-y-2-
yl group, metquin group or cyclohexylamino 1.
(represents a carbonyl group): However, in a compound.

At the same time,) When Ll is a hydrogen atom and Ca, b, C and d are 0, (1) G is a carboxyl group, methoxycarbonyl group, ethoxycarbonyl group, hydroxymethyl group: 1-hydroxy, ethyl group, 2 -Hydroxyethyl group or methylthioethyl group, or a compound in which (-)G and G' each represent a methyl group.

(i) In formula (■), X represents a hydrogen atom or a chlorine atom, and 1 is a hydrogen atom: a nitrone group: an alkyl group having 1 to 4 carbon atoms: an unsubstituted chlorine or fluorine atom; a substituted C1-C4 alkylcarbonyl group; or a C2-substituted alkylcarbonyl group;
represents an alkenylcarbonyl group of 1 to 4, Q and 1,
5-pentamethylene or the following formula: (wherein A', E', G', L' and M' can also be hydrogen atoms;
' is also a C1-C4 alkyl group or two adjacent substituents A', R', G', L
' and M' represent the bond between the two carbon atoms to which they are bonded; A, E, G, L and M also represent hydrogen atoms; A, i5. IQ of Q, L and M is also a carboxyl group: a C1-C4 alkoxycarbonyl group: a C1-C4 alkyl group which is unsubstituted or monosubstituted with a hydroxyl group or a C1-C4 alkylthio group; The symbols a and b represent groups.

2@ of C and d is 0 and the other two represent Fio or 1; or kLi and G together represent a trimethylene bridge and a, b, c and d represent 0). 1 to 3 linear or branched aliphatic radicals are represented by Table 4L<H-CN (wherein, an alkali metal cation, R'' is a hydrogen atom; a chlorine atom or a carbon atom number of 1 to a C1 -C4 alkyl group which is unsubstituted or monosubstituted with 4 alkoxy groups; or a C2 -C4 alkenyl group, kL"Vi
a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms,
h” is a hydrogen atom; an amino group; a hydroxyl group: a C1-C4 alkyl group unsubstituted or monosubstituted with a C1-C4 alkoxy group; or a C2-C4 alkynyl group, carbon Number of atoms: 1 to 4
represents an alkoxy group or a 7quaalkylaminocarbonyl group having 3 to 6 carbon atoms), provided, however, that when W is a hydrogen atom and a, b, c and d are 0 in the compound, , (1) G is a carboxyl group; an alkoxycarbonyl group having 1 to 4 carbon atoms; or an alkyl group having 1 to 4 carbon atoms monosubstituted with a hydroxyl group or an alkoxythio group having 1 to 4 carbon atoms, or (I) A compound in which G and G' both represent an alkyl group of 1, A having 1 carbon atom.

Bacteria In formula I, X represents a hydrogen atom or a chlorine atom, and 1 is a hydrogen atom or a nitroso group.

Methyl group, methylcarbonyl group, ethylcarbonyl group,
A vinylcarbonyl group, a chloromethylcarbonyl group, a trichloromethylcarbonyl group or a trifluoromethylcarbonyl group; ' is a hydrogen atom or person #, gZ G', Ll and M'
one of which also carries a methyl group, or two adjacent substituents A'.

E', G', L' and M' and M' represent the bonds between the two carbon atoms to which they are attached; A.

E, G, L and M are hydrogen atoms or A, E.

One of G, L and M also represents a carboxyl group, a methoxycarbonyl group, an ethoxycarbonyl group, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group or a 2-methylthioethyl group, and the symbol Two of a, b, c, and d are 0, and the other two represent 0 or 1 [2; Or W and G together represent trimethylene, and a.

b, c and d represent 0) having 1 to 3 carbon atoms
Straight-chain or branched aliphatic RA CONB-Ban...
or -CN (where sand is sodium cation, l
C is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, 2
- Chlorethyl group, 2-methoxyethyl group, allyl group or prop-2-ynyl group, R1 is a hydrogen atom, methyl group or cyclohexyl group, R1@ is a hydrogen atom,
(represents an amino group, a hydroxyl group, an alkyl group having 1 to 3 carbon atoms, a 2-methoxyethyl group, a buty-3-beny-2-yl group, a methoxy group, or a cyclohexylaminocarbonyl group), provided that in the compound Simultaneous vc R
' is a hydrogen atom. When a, b, c and d are 0, (1) G is a carboxyl group, a methoxycarbonyl group,
Ethoxycarbonyl group, hydroxyethyl group, 1-hydroxyethyl group.

A compound in which a 2-hydroxyethyl group, a 2-methylthioethyl group, or (-)G and ``G'' both represent a methyl group.

(+) In formula I, X represents a hydrogen atom or one chlorine atom, and R1 is a hydrogen atom, a nitrone group, a methyl group, a methylcarbonyl group, an ethylcarbonyl group, a chloromethylcarbonyl group, a trichloromethylcarbonyl group, or a trifluoro Methyl carbonyl group; QFit,
s-pentamethylene or the following formula: (wherein A', E', G', L' and M' are hydrogen atoms or A', g', G', L' and M
′ also has a methyl group, or two adjacent f
Lllll! Basic AI.

g', G', L' and M' represent the bonds between the two carbon atoms to which they are bonded: A l h t
('IL and M are hydrogen atoms or A, g
, G , L and M also represent a carphokyl//l group, an etoyaccarbonyl group, a methyl group, a hydroxyethyl group, a 1-hydroxyethyl group or a 2-methylthioethyl group, and the symbols "tbtC and 2 of d one is 0 and the other two represent 0 or 1; or bl and q
together represent a trimethylene bridge and a, b, c and d represent 0) represents a straight-chain or branched aliphatic radical having 1 to 3 carbon atoms;
0OR Hatake, -CONR"R'・4L (d-CN (in the formula,
ni&1 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a 2-chloroethyl group, a 2-methoxyethyl group, or an allyl group, 6 is a hydrogen atom, a methyl group or a cyclohexyl group, and W@ is a hydrogen atom , amino group, hydroxyl group.

(represents an alkyl group having 1 to 30 carbon atoms, 2-, methoxyethyl group, buty-5-beny-2-yl group, methoxy group or cyclohexylaminocarbonyl group), but at the same time in the compound ec kLj When is a hydrogen atom and a, b, c and d are O, (1) GFi carboxyl group, ethoxycarbonyl group, hydromethyl group, 1-hydroxyethyl group or 2-methylthioethyl group, or # '1(i) A compound in which G and G' both represent a methyl group.

- In formula I, X is a hydrogen atom, Bi is a hydrogen atom or a methyl group, QFi is the following formula:
- and M represent a hydrogen atom, or one of A, B, G, L and M also represents a methyl group, hydroxymethyl group, 1-hydroxyethyl group or 2-methylthioethyl group, and the symbols a, b, c and d two of them are 0 and the other two represent 0 or FiI; or iiR" and O together represent a trimethylene bridge and a, b, c and d
represents a C1-C3 algylene radical, where Z is -COOH, a C1-C4 alkyloxycarbonyl group, -COO-CH.

CI%OCR, or -CN, but with the proviso.

A compound in which when K h' is a hydrogen atom and a, b, c, and d are 0, G represents a hydroxymethyl group, a 1-hydroxyethyl group, a 1-hydroxyethyl group, and a Fi2-methylthioethyl group.

(n) In formula I,
During the ceremony.

1 represents a hydrogen atom, an alkyl group or an allyl group having 3 to 3 carbon atoms, and W and h'' represent a hydrogen atom.

Particularly preferred compounds are: methyl N-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenyl]-3-aminopropionate, methyl N-[2-nitro-5-[2- Chlor-4-trifluoromethylphenoxyc)phenyl]-4-amino n-butyrate, inglovir N-[
2-Nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenyl]-3-aminopropio*-)
, ethyl N-(2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenyl]-5-aminopropione-), N-(2-nido'a-s-(2-chloro-4- trifluoromethylphenoxy)phenyl]-
3-aminopropionic acid, N-(2-nitro-5-(2
-chloro-4-trifluoromethylphenoxylphenyl]-4-ami/-n-butyric acid, 5-(N-(2-nitro-5-('2-cros, -4-)IJ fluoromethylphenoxylic acid) phenyl) ~aminoco-propionamide,
Allyl N-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenyl]-3-aminopropionate.

Compounds of formula I are:

ia) The following formula I: (wherein X is the same as defined in Formula I).

A layer of the following formula: is reacted with a compound of formula I (wherein -t Q and Z are the same as defined in formula I) in the presence of a base.

(b) A compound of the following formula PI: (wherein X is the same as defined in formula I and D represents an leaving radical) is added to the following formula I: (same as the definition in ①), or

(c) The following formula V: (where X, Q and Zvi are the same as the definition of formula I, TFi
(representing a hydrogen atom or a nitro group) is reacted with an acid anhydride or an acid chloride, and if T is a hydrogen atom, the resulting reaction product is nitrated;
is an alkylcarbonyl group having 1 to 4 carbon atoms, or 1d) of the following formula ■: (wherein, X is the same as defined in formula I, Hal represents ).logen atom) The compound is reacted with a compound of the following formula (1) (wherein, nitration of the reaction product of i4', Q and 2 as defined in formula I) or.

(e) Formula V (wherein, X , Q , Z
H (same as above '9) is reacted with a corresponding alkylating reagent, and 1 in formula I has 1 to 4 carbon atoms.
(f) Optionally, by converting a compound of the formula Z in which Z is a carboquinyl group into the corresponding salt, ester, amide, ketone or nitrile by a method known per se. It will be done.

The starting compounds of the formulas i, m, *, v, w, ■, ■ and ■ are known or can be obtained by methods analogous to known methods.

Manufacturing variants (a), (b), (c), (d)
And the reaction according to (e) is.

The reaction can be carried out in the absence of a solvent or in the presence of a VC-inert solvent or diluent.

Preference is given to using organic solvents, such as low molecular weight alcohols, ketones such as methyl ethyl ketone or dimethyl boramide, dimethyl sulfoxide or chlorinated hydrocarbons, ethers or aromatic hydrocarbons. Two reaction temperatures range from FiO℃ to 2DO'C, 2o0
The temperature range is preferably from 100°C to 100°C.

Examples of suitable bases include Shiteha, KOH, 'Na0CH,.

K, CO, potassium 5-butyrate, or an organic base such as triethylamine.

Examples of suitable leaving radicals I) in production variant (b) include halogen atoms, methoxy groups, 2-chloro-4-
) IJ fluoromethylphenoxy group or 2,6-
It is a dichloro-4-triple omethylphenoxy group.

Suitable alkylating reagents include the corresponding alkyl halides or alkyl sulfnites.

Nitration of the reaction product represented by formula (2) is carried out using commonly used nitration mixed acids 1, such as a mixture of 11191 acid and nitric acid,
This is carried out in a manner known per se by treatment with a mixture of concentrated ammonium and alkali nitrates.

For application as a descaling agent, desiccant or defoliant,
The compounds of the formula ■ are used in unmodified form or preferably with excipients customary in formulation technology and can therefore be prepared as emulsion concentrates, directly sprayable or dilutable solutions, diluted by known methods. emulsion, penetrating powder, i
It is formulated into T-soluble powders, powder tablets, and capsules, such as in polymeric materials. As with the nature of the composition, the method of application, such as spraying, atomizing, powdering, spraying or spraying, will be selected depending on the object of application and the environment in which it is prevalent.

Formulations, i.e. compositions containing a compound of formula I (active ingredient) and suitable solid or liquid additives, or Ifi formulations, can be prepared in a known manner, e.g. by combining the active ingredient with fillers such as bath vehicles, solid carriers and suitable solid or liquid additives. Surface-active compounds (surfactants)
It is prepared by mixing and/or grinding in a colander.

Suitable solvents are aromatic hydrocarbons, preferably 8 to 12
fractions containing carbon atoms, such as xylene mixtures or substituted naphthalenes, phthalate esters such as dibutyl phthalate or dioctyl phthalate, aliphatic hydrocarbons such as cyclohexane or paraffin, ethanol,
Alcohols, glycols and their ethers and esters such as ethylene glycol monomethyl ether and monoethyl ether; ketones such as cyclohexanone, strong polar solvents such as N-methyl-2-pyrrolidone, dimethylsulfoxide or dimethylformamide ; and epoxidized vegetable oils such as epoxidized coconut oil or soybean oil; Mata is water.

The solid carriers used, for example for dusts and dispersible powders, are the usual mineral fillers such as calcite, talc, kaolin, montmorillonite or attapulgite. Highly dispersed silicic acid or highly dispersed polymer adsorbents can also be added to improve the physical properties. Suitable granular adsorptive carriers are porous, such as pumice, crushed brick, sepiolite-studded bentonite, and suitable non-absorbent carriers are materials such as calcite or sand. Furthermore, a very large number of inorganic or organic pre-granulated substances can be used, such as in particular dolomite or plant residue powders.

Depending on the nature of the compound of formula I to be formulated, suitable surfactant compounds and V1 nonionic, cationic and/or anionic surfactants with good emulsifying, dispersing and wetting properties. becomes.

The term exclusive surfactants Vi is also understood to include mixtures of surfactants.

Suitable anionic surfactants can include both water-soluble soaps and water-soluble synthetic surfactant compounds.

A suitable soap is high-grade fat! Alkali metal, alkaline earth metal or unsubstituted or substituted ammonium salts of (0,6-Cゎ), e.g. sodium oleic acid or stearic acid or natural fatty acid mixtures obtained from e.g. coconut oil or tallow oil. salt or potassium salt. Fatty acid methyltaurine salts are also commonly used.

However, so-called synthetic surfactants are more frequently used, especially aliphatic sulfonates, aliphatic sulfates, diphonates of benzimidazole derivatives or alkylarylsulfonates.

Aliphatic sulfonates or sulfates are usually alkali salts,
in the form of alkaline earth metal salts or unsubstituted or substituted ammonium salts and having an alkyl group of 8 to 22 carbon atoms, which also contains an alkyl part of an acyl group;
Namely, likunin sulfonic acid, dodecyl sulfate ester, is the sodium or calcium salt of fatty alcohol sulfate ester obtained from natural fatty acids. These compounds also include aliphatic alcohol/ethylene oxide adducts and salts of sulfonic acids. The sulfonated benzimidazole derivative preferably contains two sulfonic acid groups and one fatty acid group having 8 to 22 carbon atoms. Examples of alkylarylsulfonates are dodecylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid or sodium naphthalenesulfonic acid/formaldehyde condensate.

Chill with calcium or triethanolamine salt.

Corresponding phosphates, such as the salts of the phosphoric acid esters of p-nonylphenol and 4 to 14 moles of ethylene oxide, are also suitable.

Preferred nonionic surfactants are aliphatic or cycloaliphatic alcohols, or polyglyconyl ether derivatives of saturated or monosaturated fatty acids and alkylphenols, which have 3 to 50 glycol ether groups (fatty Group) 8 to 20 carbons in the hydrocarbon moiety
ff child and alkyl moiety of alkylphenol K 6 r
It has 18 carbon atoms. .

Further suitable nonionic surfactants are polyethylene diamine and polypropylene glycol, ethylenediamine polypropylene, pyrene glycol and hyalkyl chains with 1 to 10
20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups.

These compounds usually contain 1 to 5 glycol units per propylene glycol unit.

Typical examples of nonionic surfactants are nonylphenolbolyethoxyemenol, castor oil bolyglycol ether,
These are polypropylene/polyethylene oxide adduct, triptylphenoxoboriethoxyethanol, polyethylene glycol and octylphenoxypolyethoxyethanol. Fatty acid esters of polytoxyethylene sorbitan, such as polyoxyethylene sorbitan trioleate, are also suitable nonionic surfactants.

Cationic surfactants may be N-substituted such as at least one C8-C22 alkyl group and another substituent such as lower alkyl, benzyl or lower hydroxide. @Quaternary ammonium salts containing sialkyl groups are preferred. The salts are preferably in the form of halides, methylsulfate or ethylsulfate, such as stearyltrimethylammonium chloride or penzyldi(2-chloroethyl)ethylammonium bromide.

Surfactants commonly used in formulation technology are described, for example, in the publications listed below. : "Mc Cutche's Detergents and Emulsifiers Annual"
o6s Detergent and Emulsif
iersAnnual), MC Publishers, Ringwood, New Chassis, 1980
], and Sisely and Woo
d) “Encyclopedia of Surfaces”
Active Agents” (Encyclopeded
ia of 5 surface Active Agent
ts), Chemical Publishing, New York, 1980].

Agricultural compositions usually have a content of 11 to 99%, preferably α
Formulas for 1 to 95! Compounds represented by, 1 to 9
99 inches, preferably 99.8. % to 5. of solid or liquid additives, and from 0 to 25, preferably [7
It contains 0.01 to 25.0% surfactant.

Preferably, the weight product is formulated as a concentrate; the end consumer will normally use a diluted formulation.

The composition may also contain other additives such as stabilizers, defoamers, viscosity modifiers, binders and tackifiers, as well as fertilizers or fungicides or other active ingredients to obtain specific effects. can be included.

The novel compounds of formula I exhibit a herbicidal, in particular marked selective herbicidal activity, against weeds in various cultivated crops, preferably monocot crops, in particular wheat, barley, rye, oats, sugar corn, maize and rice. Shows activity. The compound of formula (2) is active in wheat, barley and rice crops. Formula summer compounds can be used for pre- and post-emergent control of weeds. The compounds of formula 1 or compositions containing them are particularly suitable for the post-emergence control of weeds in soybean crops. However, a particularly preferred area of use is the selective control of weeds in cultivated crops, in particular dicotyledonous weeds during cereal planting, preferably pre- but also post-emergence.

Particularly useful compounds for this practical use are those in which X and R' are hydrogen atoms, Q is an ethylene or trimethylene bridge, and 2 is -COORI or -CONR"R"
(in the formula, R- represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R9 and R1 represent a hydrogen atom), especially methyl N-[2-nitro-5-(2-chloro -4-trifluoromethylphenoxy)phenyl-3-aminoprobionate, methyl N-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenyl)-4-amino-n-butyrate, isopropyl N-[2-nitro-5-(2
-chloro-4-trifluoromethylphenoxy)phenyl]-3-aminopropionate, ethyl N-(2-
=) rho5-(2-chloro-4-)IJfluoromethylphenoxy)phenyl]-5-aminopropionate, N-[2-nitro-5-(2-ri°rho-4-trifluoromethylphenoxy) N-(2-nitro-5-(2-chloro-4-
trifluoromethylphenoxy) phenylcy 4-amino-n-butyric acid and 3-(N-(2-nitro-5-(2
-chloro-4-)IJfluoromethylphenoxy)phenyl]-aminopropionamide.

The compounds of formula I and the compositions Fi containing them are also suitable as drying and defoliating agents for cotton and potato crops. Treatment of plants can be done before harvest, and the exact time of treatment depends on a variety of factors, such as the year and condition of the crop and the climate.

It is convenient to treat crops about two weeks before harvest.

Compounds of formula I suitable for this area of use are X
and R1 is a hydrogen atom, Q is an ethylene or trimethylene bridge, and 2 is a methoxycarbonyl group or an allyloxycarbonyl group, especially methyl N-[2-
Nitro-5-(2-chloro-4-) IJfluoromethylphenoxy)phenyl]-4-amino-n-butyrate, methyl N-[2-nitro-5-(2-chloro-4
-trifluoromethylphenoxy)phenyl]-3-aminopropionate and allyl N-[2-nitro-
5-(2-chloro-4-trifluoromethylphenoxy)phenyl]-3-aminopropionate.

Production Examples Example 1: N-[2-nitro-5-(2-chloro-4-
3,4-dinitro-2 of trifluoromethylphenoxy)phenylcou 4-amino-n-butyric acid (compound 1) 9f
'-Chloro-47-trifluoromethyl-diphenyl ether in 20m/dimethyl sulfoxide, 3-water,
5.1 p of 4-amino-n-butyric acid and 5 ml of 30%
Stir into aqueous sodium hydroxide solution. The mixture is manually heated to 110° C. to complete the waste heat reaction. The reaction mixture is then poured into about 500 ml of water and extracted once with about 100 liters of toluene. The aqueous layer thus purified is acidified with glacial acetic acid and extracted with ethyl acetate. If the combined ethyl acetate solution is concentrated to about 301 and the residue is recrystallized from about 10 pm+/- hexane, 9f of N-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy) can be obtained. ) phenyl]-4-aminobutyric acid with a melting point of 126-127°C.

Example 2: Methyl N-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenylcy 4-amino-n-butyrate (compound 2) 8f N-[2-nitro-5- (2-chloro-4-trifluoromethylphenoxyraphenyl]-4-amino-
Dissolve n-butyric acid in 50w1 methanol, then 1
0M1 concentrated sulfuric acid is slowly added. The reaction mixture is allowed to stand for several hours, then poured onto ice, made alkaline with sodium hydroxide solution and extracted with toluene. The toluene extract is washed with water until it becomes neutral and substantially condensed under reduced pressure. If the residue is recrystallized from hexane, 6t of methyl N
-[2-Nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenylcy 4-amino-n-butyrate is given as melting point 60-62°C.

Example 3: 5-[N-(2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenyl)amii]propionamide (compound 33) 88f of N-[2-nitro-5-( 2-chloro-4-trifluoromethylphenoxy)phenyl]-3-aminopropionic acid (compound 3) was added to 34.3 l of 500 t/methylene chloride containing 125 l of triethylamine.
Add at ℃. While stirring, 22.817 ml of methyl chloroformate is added over 30 minutes and stirring is continued at -10° to -20°C. After 2 hours, the ammonia solution of 4011/O is applied, the reaction mixture is warmed to room temperature, the mixture is then washed with water, and the organic layer is concentrated. The residue is recrystallized from ethyl acetate/hexane. The product has a melting point of 137-138°C.

Example 4: Methyl N-acetyl-N-('2-nitro-5-(2-chloro-4-) Q fluoromethylphenoxy,) phenylcy 4-amino-n-butyrate (compound 54) 109 methyl N- [2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenylcy 4
-Amino-n-butyrate (compound 2) is refluxed in 301 acetyl chloride until hydrogen chloride evolution is complete. Excess acetyl chloride is distilled off under reduced pressure to give the title bile compound in quantitative yield. ? ID-t5457° Formula I listed in Table 1 together with the compounds of Examples 1 to 4
Compounds below O can be prepared by similar methods.

Examples of formulations of liquid active ingredients of formula I (CH = heavy weight)
5. Emulsion concentrate i) b)
c) Compounds in Table 1 25% 40ts50 Ticyclohexanone - 159G 2
011 Xylene Mixture 65 cm 25 cm 20 - Emulsions of the required concentration can also be prepared by diluting concentrates of this type with water.

Melon solution a) b) c) d)
＼ Compounds in Table 1 80% 10% 5% 95%4
0G-70% -- N-methyl-2-pyrrolid/-20 ---Epoxidized coconut 7 oil --1% 5% ligroin (boiling range --94% -160~190°C) The solution is fine Suitable for application in the form of drops.

7% granules a) b) Compounds in Table 1 5% 10% Kaori 7
94% - Highly dispersed silicic acid 1 - Acpulgide - 90% The active ingredient is dissolved in methylene chloride, the resulting solution is sprayed onto the carrier and the solvent is then evaporated under reduced pressure.

a) Powder a) b) Compound of Table 1 24 5% Highly dispersed silicic acid 1% 5% Talc 97% - Kaolin - 90% Powder that can be used as is is obtained by homogeneously mixing the carrier and the active ingredient. Obtained from K.

9 Wettable powders O) b) C) Compounds in Table 1 25% 50% 75% Sodium ligninsulfonate 5% - Sodium lauryl sulfate 3% -51 Highly dispersed silicic acid 5% 10% 10-9 olin
62 27% - The active ingredient is mixed well with the excipients and the compound i is thoroughly milled in a suitable mill. When diluted with water, a hydrating agent is obtained which can be made into a suspension of the desired concentration.

1α Emulsion concentrate Compounds of Table 1 10 Thioxide 4 to 5 mol) Cyto 56 mol) Cyclohexanone 60% xylene mixture 50 t An emulsion of the required concentration can be obtained by diluting this concentrate with water.

11. Powders a) b) Compounds of Table 1 5T 8Ttalc 95T - Kaolin -92T The ready-to-use powder can be prepared by mixing the active ingredient with the carrier and milling the mixture in a suitable mill. More can be obtained.

12. Extruded Granules Compounds of Table 1 10% Sodium Lignosulfonate 2 Thi-Calphoki/Mef Cellulose 1 Thikaolin 87 The active ingredients are mixed and milled with the additives and the mixture is subsequently moistened with water. The mixture is extruded and dried in a stream of air.

15 Coated granules a) Compounds in Table 1 5% Polyethylene glycol 200 3%
- Kaolin 94%.

The finely ground active ingredient is applied evenly to the polyethylene glycol-moistened kaolin in a mixer. In this way, a non-dusty edible granule is obtained.

14. Suspension concentrate Compounds in Table 1 40% Ethylene glycol 10T.

15 moles of oxide) Sodium ligninsulfonate 10% carboxymethylcellulose 1% 37% formaldehyde aqueous solution α2% water
52% Finely ground active ingredient is homogeneously mixed with additives.

A suspension concentrate is obtained in this way, and by dilution with water a suspension of the desired concentration is obtained.

Biological Examples Example 15: Pre-emergence Spraying Herbicidal Effect (Germination Inhibition) Test Immediately after sowing the plant seeds in sowing trays in the greenhouse, the soil surface was treated with 254 water of a compound of formula I. It was treated with an aqueous dispersion obtained from a Japanese preparation. The application concentration was 4 Kf of active ingredient per hectare. The seeding trays were placed in a greenhouse at a temperature of 22-25 °C and a relative humidity of 50-70 °C, and the test results were evaluated after 3 weeks using the following criteria: 1 = no germination or no germination. Dead Plants 1 2-5 = Very Severe Effect 4-6 = Moderate Effect 7-8 = Slight Effect 9 = No Effect (as untreated control plants) The compound of formula 1 is highly effective in this test It is. Table 2 summarizes the effects on weeds of the genus Sinapis, Seteria, and Stellia.

Table (Continued) I (Continued) Example 16: Pre-emergence spraying herbicidal action (germination suppression) Example 1
On a number of cultivated plants and weeds under the conditions described in 5.
Tests were conducted using concentrations of 4 Kg active ingredient/ha and 2 Kg active ingredient/ha. The results are in Example 1
Judgment was made according to the evaluation used in 5.

The compounds of formula I have good selective herbicidal action in this test. The results are shown in Tables 3 and 4.

Hawk No Example 17 Two Post-Emergence Spraying, Herbicidal (Contact Weeding) Tests 4 to 6 days after germination of weeds, two of the compounds of formula I were applied.
The aqueous dispersion obtained from the formulation as a Permanent Agent No. 54 was applied at a rate of 4 Kg active ingredient/ha. Plants were left at 24-26° C. and 45-60° relative humidity.

The test was judged after 15 days according to the evaluation used in the pre-emergence spray test (Example 15).

As can be seen from the results shown below, compounds of formula I are highly effective in this test.

Table 5 (continued) Table 5 (continued) Example 18 Post-emergence spraying herbicidal action (contact weeding) Example 1
A number of cultivated plants and weeds were tested using a concentration of 1 α5 Kg active ingredient/Tuctar under the conditions described in Section 7. The results were determined according to the evaluation used in Example 15.

The compound of formula I performs very well in this test, as can be seen from the results below.

Even at low concentrations of the compound of formula I, the following comparisons, i.e. values) Table 6 α5 active ingredient/hectare, (b) α25
To? A comparison of a number of compounds in active ingredient/ha and (c) α12Kf active ingredient/ha has a good or selective herbicidal action.

Example 19: Desiccation and defoliation Deltapine (De 1 ptne > m cotton plants were grown in earthenware pots filled with a mixture of soil and beets in a greenhouse. After 12 weeks (flowering begins) ), a water-bathable composition of the compound of formula (1) is applied to plants at 150,5
00 and 600f active ingredient/ha (500t/
hectare) equivalent to #darkspraying.ru. Untreated plants were used as controls.

The test evaluation was based on the degree of leaf fall (14 days after the application of the active ingredient).
The results were determined based on the degree of defoliation (chi) and degree of dryness (dryness of leaves remaining on the plant is expressed in chi). Road leaf chips are always included in dry chips. The compounds of formula I had a good effect in this test, in particular as seen from Table 8, compound 2.8
and 48 were good.

Table 8 The above compounds are also particularly active in corresponding tests on potato plants.

Patent applicant Teper Geigy 'Akchen Gesellschaft (or one person) Continued from page 1 101/34 6956-4H103/
183 7375-4H103/34
7375-4H103/90
7375-4H1091007162-4H 121/43 7731-4H121/
453 7731-4H149/42
7162-4H15310177142
-4H 1531097142-4H Priority claim 06/7/1982 ■Switzerland (C'
H)■3504/82-7

Claims (1)

[Scope of Claims] (1) The following formula I; 1 [wherein, 4 alkyl group, C21 to 4 alkenyl group, C1 to C4 alkylcarbonyl group or carbon! An alkenylcarbonyl group having 2 to 4 atoms, which is unsubstituted or substituted with one or more halogen atoms, Q is an atom or an alkyl group having 1 to 4 carbon atoms; , or substituents A', E', G' in contact with iI of 2@l,
L' and M' represent the bonds between the 2@ carbon atoms to which they are bonded; A, E, G, L and M are hydrogen atoms or 111 or 2@ of A, E, G, L and M; ga mata one OR” Knee SR3;-COOR'
;C1-C4 alkyl group, or -OR'
,, -8R' or -COOR7 substituted lI prime atom number table 4 ak Q k group (,R'',
R'', R', R'', R number R' represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; a + b + Cb and d represent 0 or 1; or R1 and G together represent trimethylene, and a, b, c and d represent a C 1 -C 5 aliphatic radical or a branched aliphatic radical; and Z is a group; -COOoMP , -COORri, -C
O8 田-CONR'RIL', -CUR phoenix or -CN (in the formula. ylee is a cation '2. R' is a hydrogen atom;...unsubstituted by a rogen atom, cyano or an alkoxy group having 1 to 4 carbon atoms) or a substituted C1-C8 alkyl group; a C2-C8 alkenyl group; or a C5-C8 alkynyl group, where R9 is a water bulk atom, and a C1-C4 alkyl group; or a cycloalkyl group having 3 to 6 carbon atoms.
RIG is hydrogen atom; amino group; water 114; number of vertical atoms is 1
an alkyl group having 1 to 4 carbon atoms which is unsubstituted or substituted with an alkoxy group having 1 to 4 carbon atoms; or an alkynyl group having 2 to 4 carbon atoms; an alkoxy group having 1 to 4 carbon atoms; or an alkyl group having 3 carbon atoms to 6 cycloalkylaminocarbonyl groups, and R11 is a water atom; or carbon unsubstituted or substituted with an alkoxy group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 atoms 1) However, in the compound, the same WI
fKR' is a hydrogen atom, and a, b. c J-; yo U d ka0 throat is (ll G
+t -OR,1;-COOR,'; or-
〇R', -8R' or -COOR7-substituted alkyl group having 1 to 4 carbon atoms, or +if
) G and σ both represent an alkyl group having 1 to 4 Km prime atoms. ] A compound represented by (2) In formula (■), X represents a hydrogen atom, a salt atom, a fluorine atom, or a bromine atom, and P represents a hydrogen atom, a nitroso group, an alkyl group having 1 to 4 R atoms, or one or more R atoms. unsubstituted or mo-substituted by a halogen atom of
↓C-substituted alkylcarbonyl group having 1 to 4 carbon atoms, Q is the following formula; (wherein, A', E', G', L' and M'
is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms,
or two adjacent substituents A', E', G'. [and y represent the bond between the 2 fll carbon atoms to which they are bonded; At E, G, L and M are water bulk atoms or 1 of A, E, G, J, # and M
-(JR2; -8R''. -COOR4; C1 -A alkyl &
;17. :! i -0Rs, -8R'moL < 4
! -COOR7K, one substituted alkyl 2I having 1 to 4 atoms (R 1t*, R4, R1
, R@ and R7 represent an alkyl group of the hydrogen atom; b, C and d represent 0 or 1; or Bj and G together represent a trimeprene bridge, and a,
b, c and d represent 0) C 1 -C 5 straight or branched chain -COORI, -CON・R
”MoL < BarCN (In the formula, the first cation is R
8 is a water line atom; halogen atom or 1 carbon atom (
- C1 -C4 alkyl group unsubstituted or substituted by -4 alkoxy group; C2 -C4 alkenyl a1. R' is a hydrogen atom, number of carbon atoms is 1
argyl group having 3 to 4 carbon atoms; or 3 to 6 carbon atoms;
σ) A cycloalkyl group, R10 is a hydrogen atom; an amino group; a hydroxyl group, the number of carbon atoms is 1 or more, and the number of carbon atoms is 1, which is non-1f bent or substituted with 1 by the alkoxy group of . Alkyl group; or alkynyl group having 2 to 4 carbon atoms; alkoxy group having pH to 4 carbon atoms;
Or, the number of carbon atoms is 6 (・shi6, cycloalkyl amine 7 carbonyl group is shown), but in the compound, K R'' is a hydrogen atom, and a, b, c
And when d is 0, +1 a is 100OR';
Or +'! -0R1. -8R. or -COOR' An alkyl group having 1 to 4 atoms in the R group substituted by t from K, or (1G and d both being an alkyl group having 1 to 4 carbon atoms.) Claim 1 (3) In the formula r, X represents a hydrogen atom, a chlorine atom, a Huhne atom, or a bromine atom, R is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and Q is a compound of the following formula: , A,, E, G, L and M are hydrogen atoms 4L<&!A, E, G, L# and M (7311vA
Or two are also one OR”;-8R”;-COO
R'; C1-C4 alkyl group; or -
0R5゜-S R' or -COOR'-substituted carbon atom H112: Ishi4]7#-? A-group (R'', R''lR4, R&, R6 and R7 are 1 g water atom or an alkyl group having 1 to 4 carbon atoms)
'kff; a, b, c and d are O or 1
or R1 and G together represent a trimethylene bridge and a, b, c and d represent O)
represents a fi chain or branched alkylene radical of carbon atoms fi1 to fi5, and Z is -CN;
J is a metal cation, t is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, R''# and R10 are a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, y, R1
1 represents an alkyl group having 1 to 4 carbon atoms substituted with an alkoxy group having 1 to 4 carbon atoms -[)
However, in the compound, when R1 is a hydrogen atom and a, b, c, and d are O, G is 10R2
; C0OR'; or -OR', -8R"
or 1 carbon atom substituted by -COOR'
The compound according to claim 1, which is an alkyl group of 4 to 4. (4) In 2I, X represents a hydrogen atom, a chlorine atom, a fluorine atom, or a bromine atom, and R1 is also a hydrogen atom.
, or an alkyl group having 1 to 4 carbon atoms, Q is of the following formula: (wherein A, E, G, L and M are hydrogen atoms or one of A4F4G, I and M is also -OH -CUOR'; alkyl group having 1 to 4 carbon atoms; t'!-OR', -8R'4L<42-C0
OR' KyoQflllll+ represents an alkyl group having 1 to 4 carbon atoms (R8゜R3, R', R', R' and R7 are hydrogen atoms or alkyl groups having 1 to 4 carbon atoms); s, c and d, 21
solid is 0, the other 2gA represents 0 or 1; or al and G represent -WjiK trimethylene bridge, and the number of carbon S atoms is 1 (
・Shi5's linear chain is also a branched alkylene radical e
■ Fit into Al 1, Z is -COOMe, -COOR@,
-CUR" or -CN (in the formula, the end is a gold cation. R5°↓ hydrogen atom or alkyl group having 1 to 4 carbon atoms; all is a carbon atom substituted with an alkoxy group having 1 to 4 carbon atoms; (represented by an alkyl group of numbers 1 to 4), provided that in the compound, when R1 is a hydrogen atom and a, b, c and d are 0,
G is -OR";-COOR'; 4 L < f-
The compound according to claim 1, wherein J -OR', -8R'4 L< is a C1-C4 alkyl group substituted with -COUR7. (5) In formula I, X represents a hydrogen atom or a chlorine atom, and R1 is a hydrogen atom, a nitroso group, a methyl group,
Methylcarbonyl group, ethercarbonyl group, vinylcarbonyl group, chloromethylcarbonyl group, trichloromethylcarbonyl group or trifluoromethylcarbonyl group; Q is the following formula: (wherein A', r, G', υ and M' is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. Or 2@ adjacent substituents A', Bi, G'. L' and M' are two carbon atoms to which they are bonded (・
Represents a bond between atoms: A, E, G, L, and M are hydrogen atoms, or one of A, E, G, L, and M is also one OR'';-8R''C0UR'; carbon number 1 to 4 alkyl group: or -OR', -8
R' 4 L <Ha=-COOR'K yoQ-substituted alkyl group having 1 to 4 carbon atoms (R1°R',
R4, R1, R.OJ: hi R'ha water 18 i child 4
L < C 1 to 4 alkyl group); a, b, c and d represent 0 or 1; or L' and G together represent trimethylene;
and a, b, c and d represent 0) represents a straight chain or branched aliphatic radical having 1 to 5 carbon atoms, and Z is -coo"d', -cooRl, -
coNR1R&64 L < haLCN (where Mt represents a cation, a hydrogen atom; a C1-C8 alkyl group substituted with a rogen atom or a C1-C4 alkoxy group; an alkenyl group having 2 to 8 carbon atoms, or an alkynyl group having 5 to 8 carbon atoms, where R'' is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms;
1 to 6 cycloalkyl groups. RlO is a hydrogen atom;
Amino group; hydroxyl group; C1-C4 alkyl group unsubstituted or substituted by C1-C4 alkoxy group; or C2-C4 alkynyl group; C1-C4 alkoxy group; or a 7-chloroalkylaminocarbonyl group having 5 to 6 carbon atoms), provided that at the same time in the compound [R1 is a hydrogen atom and a, b, c and d are 0
When , Ill G bar C0OR': or -
C 1 -C 4 alkyl group substituted by OR', -8R or -COOR' K, or (-
2.) The compound according to claim 1, wherein G and G' are both alkyl groups having 1 to 4 carbon atoms. (6) In formula ■, X is a hydrogen atom or a chlorine atom, R1 is a hydrogen atom or a methyl group, and Q is the following formula: (wherein, A, E, G, L and M are hydrogen atoms or A, , one of E, G, L and M is OR”
-8RI; -COOR4; Number of carbon atoms is 1. 4 alkyl group 2 or 10R--8R- or-
Number of carbon atoms substituted from coow K: 1 night, 4
Noful *A4 (R", R", R4, R1, R'
and R7 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; symbol 1. b. Two of C and d are 0, and the other two are 0 or 1v; or R1 and G represent a trimethylene bridge at -Ilji, and a, b, c, and d represent an opening. ) for straight chain or branched alkylene radicals having 1 to 5 R atoms, Table bL, z #f -co(f)
Mt, -cooRI, -coR or 10 (in the formula, MWB gold cation is substituted, R1 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and R11 is substituted by an alkoxy group having 1 to 4 carbon atoms) (representing an alkyl group having 1 to 4 carbon atoms). However, in the compound, when R1 is a carp hydrogen atom and b, c, and d are 0, G is replaced by 10RB, C0OR';, or -0R--8R, or -COOR'K. 1 to 4 carbon atoms
The compound according to claim 1, which is an alkyl group of (7) In formula I, X is a hydrogen atom or a chlorine atom, and R1 is a hydrogen atom, a nitro V group or an alkyl group having 1 to 4 carbon atoms, and 2 to 4 carbon atoms.
also alkenyl groups and C1-C4furkylcarbonyl groups. Shikake is an alkenylcarbonyl group having 2 to 4 carbon atoms, which is unsubstituted or substituted with 1 to 3 chlorine or fluorine atoms, and Q is 1,5-pentamethysugimoshi or the following formula: in which E', σ, υ and M' are hydrogen atoms or 1m of σ, L and M are also C1-C4 alkyl groups or two adjacent substituents A', g, σ, L'' and M' represent the bonds between the 2fa vertical atoms to which they are bonded, and A, E, G, L and M are water atoms or 1 of A, E, G, L and M.
also represents a carboxyl group: a C1-C4 alkoxycarbonyl group; Symbols a, b, c o and d are 2 @ 0, the other two represent 0 or 1; or R1 and G together represent trimethylene, and a. b, c and d represent 0) with 1 to 3 carbon atoms;
represents a chain or branched aliphatic radical, Z
-coO°M view-COOR'. -CON R'R'' or -CN (wherein M9 is an alkali metal cation, R1 is a hydrogen atom; a carbon atom that is unsubstituted or monosubstituted with a chlorine atom or a C1 to C4 alkoxy group ( -8 alkyl group: or an alkenyl group having 2 to 8 vertical atoms or an alkynyl group having 5 to 8 carbon atoms, R''
represents a water bulk atom, an alkyl group having 1 to 4 carbon atoms, or a 7-chloroalkyl group having 5 to 6 carbon atoms, RI
O is a hydrogen atom, an amino group, a hydroxyl group; a C1-C4 alkyl group unsubstituted or monosubstituted with a C1-C4 alkoxy group; or a C2-C4 alkenyl group, a carbon atom 8.b.C and when d is 00, (1) G is a carboxyl group; a C1-C4 alkoxycarbonyl group; or a C1-C4 alkylthio group monosubstituted with a hydroxyl group or a C1-C4 alkylthio group; The compound according to claim 1, wherein both an alkyl group, or tillG and σ both represent an alkyl group having 1 to 4 carbon atoms. (8) In formula I, X represents a water bulk atom and R1 represents a hydrogen atom. , Q connects the 1,2-ethylene bridge to Z car c -cooRl, -cosRa, -cohR9R1
0゜-CORII or -CN (where M♀ is a cation 'r%R' is a hydrogen atom: a vertical element unsubstituted or substituted with a rogen atom, a cyano group or an alkoxy group having 1 to 4 carbon atoms) an alkyl group having 1 to 8 atoms; or an alkenyl group having 2 to 8 carbon atoms; or an alkynyl group having Hs to 8 carbon atoms; R9 is a hydrogen atom; **an alkyl group having 1 to 4 atoms or an alkyl group having 1 to 4 atoms; 3 to 6 cycloalkyl group, RIG is a water bulk atom niamino group; hydroxyl group; 1 carbon atom unsubstituted or substituted with an alkoxy group having 1 to 4 carbon atoms;
an alkyl group having 2 to 4 carbon atoms; or 2 to 4 carbon atoms;
R' is a hydrogen atom; or an alkoxy group having 1 to 4 vertical atoms, unsubstituted or 2. A compound according to claim 1, which is a substituted C1-C4 alkyl group 'lk. (9) In formula I, X represents a hydrogen atom, a chlorine atom, a fluorine monoatom or a bromine atom, and R1 is a hydrogen atom,
Nitroso group or C1-C4 alkyl group, C2-C4 alkenyl group, C1-C4 alkyl group
-4 alkylcarbonyl group or 2 carbon atoms
to 4 alkenylcarbonyl groups, unsubstituted or substituted with one or more nitrogen atoms, Q is 1,5-pentamethylene or the following formula: (wherein A', E : a', t,' and M bamboo water atoms or one of A', r, σ L/ and M also carries a methyl group or 2 fm adjacent substituents AGE:
a; L' and M' represent the bonds between the two carbon atoms to which they are bonded; A, E, G, L and M are hydrogen atoms or A, E, G, L and M
One of them is also a carboxyl group, a methoxycarbonyl group,
The symbol a represents an ethoxycarbonyl group, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, or a 2-methylthioethyl group. Two of b, c and d are 0, and the other two are 0 or 1
or R1 and G together represent trimethylene machine and a, b, c and d represent 0)
Return! 1g represents a linear or branched aliphatic radical having 1 to 3 atoms, Z is -coO° -〇〇O
R'. -CONR'R1'' or -CN (in the formula, Mψ is a sodium cation, R1 is a hydrogen atom, number of carbon atoms is 1)
to 4 alkyl groups, 2-chloroether groups, 2-methoxyether groups, allyl groups or pro-2-ynyl groups, R9 is a hydrogen atom, methyl group or cyclohexyl group, R1 is a hydrogen atom, amino group, hydroxyl group, carbon An alkyl group having 1 to 5 atoms, a 2-methoxyethyl group, a but-6-y-2-yl group, a methoxy group or a cyclohexylaminocarbonyl group, provided that in the compound, At the same time KR' is a hydrogen atom and a, b
, when c and d are 0, 1llG is a carboxyl group, methoxycarbonyl group, ethoxycarbonyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, or methylthioether group, or I
The compound type according to claim 1g1, wherein MIG and σ both represent a methyl group. (G) In formula I, X represents a hydrogen atom or a basic atom, and R1 is a hydrogen atom: a nitroso group; an alkyl group having 1 to 4 carbon atoms; unsubstituted or substituted with a salt xi atom of 1 to 3 @ or a fluorine atom a carbonyl group having 1 to 4 carbon atoms; or a carbonyl group having 2 carbon atoms;
represents an alkenylcarbonyl group of 1 to 4, and Q is 1.
5-pentamethylene or the following formula: (wherein A, g, R2L' and M' are hydrogen atoms or A', E';
is also an alkyl group having 1 to 4 carbon atoms or 2
The adjacent substituents A', Bi and Z L/ and M' represent bonds between the 2g carbon atoms to which they are bonded, and A, E, G, L and M are hydrogen atoms or
, E, G, L and 141 of M are also carboxyl groups; C1-C4 alkoxycarbonyl groups; C1-C4 unsubstituted or mono-substituted with hydroxyl groups or C1-C4 alkylthio groups; 4 represents an alkyl group, and the symbol a. 2 of b, c and d are 0, other 2 @ are 0 or 1
or R1 and G together represent trimethylene, and a, b, c and d represent 0); a linear or branched aliphatic radical having 1 to 3 carbon atoms; Representation, Z is -C000M♀, -COOR
', -coNR''R1'' or -CN (in the formula, M♀
is an alkali metal cation; al is a hydrogen atom; a C1-C4 alkyl group unsubstituted or monosubstituted by a basic atom or a C1-C4 alkoxy group; or a C2-C4 alkenyl group; The group %R9 is a hydrogen atom, a C1-C4 alkyl group or a C6-C6 cycloalkyl group tIt. Rlo is a hydrogen atom; an amino group; a hydroxyl group; an alkyl group having 1 to 4 R atoms a1 to 4 unsubstituted or monosubstituted by an alkoxy group having 1 to 4 carbon atoms; or an alkynyl group having 2 to 4 carbon atoms, M, * element an alkoxy group having 1 to 4 atoms or a dichloroalkyl abanol carbonyl group having 3 to 6 carbon atoms, provided that in the compound at the same time R1 is a hydrogen atom and a, b,
When c and d are 0, (1) G is a carboxyl group; an alkoxycarbonyl group having 1 to 4 carbon atoms; or a hydroxyl group or an alkylthio group having 1 to 4 carbon atoms monosubstituted with a carbon atom group; The compound according to claim 1, wherein (0) G and G' are both alkyl groups having 1 to 4 carbon atoms. (b) In formula I, X represents a hydrogen atom or a chlorine atom, and R' represents a hydrogen atom, a nitroso group, a methyl group, a methylcarbonyl group, an ethylcarbonyl group, a vinylcarbonyl group, a chloromethyk group, a chlorine group, a trichloromethyl group Carbonyl group or trifluoromethylcarbonyl group t=; Q is 1.5-pentamethylene module or the following formula: (where x, i, σ, L' and M' are hydrogen atoms or p, σ 1 ./ and 1@28 of M' or a methyl group, or two adjacent substituents A', E'
, GSL' and M' represent the bonds between the two carbon atoms to which they are attached. HAHE, G, L and M
is a hydrogen atom or A. 1gA of E, G, L and M also represents carboxyl group, methoxycarbonyl group, ethoxycarbonyl group, methyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-
Represents a hydroxyethyl group or a 2-methylthioether group, with two symbols 1a, , b, c and d? S
l"O, the other two represent 0 or 1; or R1 and G together represent trimethylene my11', and a, b, c and d exclude O) having 1 to 30 carbon atoms; It represents a straight-chain or branched aliphatic radical, and Z is -CO^♀. -COOR', -CONR'R' or -CN (wherein Mψ is tricum othion and R1 is a hydrogen atom, having 1 to 1 carbon atom 4 alkyl group, 2-chlornibble group,
2-methoxyether group, allyl group or pro-2-
P is a hydrogen atom, a methyl group or a cyclohexyl group, aJ is a water bulk atom, an amino group, a hydroxyl group, an alkyl group having 1 to 3 carbon atoms, a 2-methoxyethyl group, a 1-d-3-yny-2-yl group, group, methoxy group or cyclohexylaminocarbonyl group), provided that at the same time in the compound R1 is a hydrogen atom and a, b
, when c and d are 0, IIJG is a carboxyl group,
A methoxycarbonyl group, an ethoxycarbonyl group, a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 2-methylthioethyl group, or (iil where G and G' represent a covalent methyl group) The compound according to item 1. In formula (2), X represents a water bulk atom or a bulk atom, and R1 is a hydrogen atom, a nitroso group, a methyl group, a methylcarbonyl group, an ethylcarbonyl group, a chloromethylcarbonyl group, trichloromethylcarbonyl group or trifluoromethylcarbonyl group; Q is 1.5-pentamethylene or the following formula: (wherein A: EGSL compound and M' is a hydrogen atom or A', BiG', I, / and one of y is also a methyl group, or a substituent A, l g
G', L' and M represent the bonds between the two carbon atoms to which they are attached; A, E, G. L and M are water bulk atoms, or one of A, E, G, L and M can also be a carboxyl group, ethoxydicarbonyl group, methyl group, hydroxymethyl group, 1-hydroxyethyl group or a < 422 + methylthioether group. Two of the symbols a, b, c and d are 0, and the other 2Il represent 0 or 1; or G'! R
” and G together represent a trimethylene bridge, and set a, b
, c and d represent 0), a straight or branched aliphatic radical having 1 to 3 carbon atoms, and Z represents -COOR', -CONR"R"° or -CN (in the formula , R1 is a water atom, an alkyl group having 1 to 4 carbon atoms, 2-chloroether M, 2-methoxyether group, or an allyl group; R'!1 is a hydrogen atom, a methyl group or a cyclohexyl group Y%R'' hydrogen atom, amino group, hydroxyl group, alkyl group having 1 to 3 carbon atoms, 2-methoxynibble group, buty-3-y-2-yl group, methoxy group or cyclohexyl ainocarponyl group)
However, when simultaneously K R'' in the compound is a hydrogen atom and a, b, c and d are 00, jljG is a carboxyl group, ethoxycarbonyl group, hydroxymethyl group. 1-hydroxyethyl group or 2-methylthio ether group, or (ii) the compound according to claim 1, wherein G and σ are both methyl groups. is the following formula: (wherein A, E, G, L jd and M are hydrogen atoms, or one of A, E, G, L and M is also a methyl group, hydroxymethyl group, 1-hydroxyethyl group or 2 - methylthioether group, symbols a, b
, C and d are 0 and the other two are 0 or 1; or R1 and G together represent a trimethylene bridge and a, b, c and d represent 0. ) represents an alkylene radical having 1 to 5 carbon atoms, Z is 1000H1 an alkyloxycarbonyl group having 1 to 4 carbon atoms, -coo-c represents a Cl OC mountain, or -〇N . However, when R1 is a hydrogen atom and abc and d are 0 in the compound, G is a hydroxymethyl group, 1-hydroxyethyl group, or 2-methylthioether group. (b) In formula I, X is a hydrogen atom, R1 is a hydrogen atom, Q is an ethylene or trimethylene bridge, z -
ts-eooR14L <barC0NFPR"('
The compound according to claim 1, wherein 1R1 represents a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, or an allyl group, and Re and R11l represent a hydrogen atom. (To) Methyl h-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenyl2
The compound according to claim 1, which is -aminopropionate. Methyl to [2-nitro-5-(2-chloro-4
-trifluoromethylphenoxy)phenyl]-4-amino-n-butyrate. Claim 1 which is αri isopropyl to [2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenyl-3-aminopropionate.
Compound described in r#. (7) Ether He[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenyl2 3
-aminopropionate, the compound according to claim @1. QI N-(2-nido-5-(2-ri-4-trifluoromethylphenoxy)phenyl)-5-aminopropionic acid, the compound according to item 1. [2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenyl]-4-amino n
- Compound 1 of Claim 13311 which is butyric acid
to iIl@3-(N-(2-nitro-5-(2-rip-4
-trifluoromethylphenoxy)phenyl)-aminoco-propionamide. (a) Allyl He [2-nitro-5-(2-chloro-
4-Trifluoromethylphenoxidinephenyl]-3-
A compound according to claim 1 which is an aminopropionate. Quaternary formula I: 1 to 1 [wherein, , they represent one or seven groups, Q is of the following formula: (wherein h', ES CS L' and M' are hydrogen atoms or C1-C4 alkyl groups, or two adjacent Substituents A', El, G: L' and M' represent bonds between the two carbon atoms to which they are bonded; A, E, G, R8 and M are hydrogen atoms or A , one or two of E, G, L and M are also -OR";-8R";-COOR'; alkyl group having 1 to 4 carbon atoms; also '@ -L)
R', -8R', < )i -C4 alkyl group substituted by -COOR'(R"
, R', R', R", Ra and R7 represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; a, b, c and d represent 0 or 1, and two or R1 and G together represent a trimethylene bridge, and a. b, c and d represent 0;
0 represents a straight chain or branched aliphatic radical; and Z is *: -coOoMt, -cooaki-C'08
R1゜-CONR'RIG, -COR'' or -CN
(In the formula, M♀ is a cation, Ra is a hydrogen atom; the number of unsubstituted or substituted halogen atoms, cyano, or C1-C4 alkoxy groups is 1)
an alkyl group having 2 to 8 carbon atoms; an alkenyl group having 2 to 8 carbon atoms; or an alkynyl group having 3 to 8 carbon atoms; Ra is a hydrogen atom, an alkyl group having 491 to 4 carbon atoms, or a cyclo an alkyl group, R10 is a hydrogen atom; an amino group; a hydroxyl group; an alkyl group having 1 to 4 carbon atoms which is unsubstituted or substituted with an alkoxy group having 1 to 4 carbon atoms; or an alkyl group having 2 to 4 carbon atoms; group, 1 to 4 carbon atoms
alkoxy group; or X atom &5I6 to 6
cycloalkylaminocarbonyl group, esite Rtt
is a hydrogen atom; or a C1-C4 alkoxy group substituted or substituted with a C1-C4 alkoxy group
represents an alkyl group), provided that in the compound,
At the same time, when R1 is a hydrogen atom and a, b, C and d are 00, (1) G is -OR'';-C(JOR';
A C 1 -C 4 alkyl group substituted with -0R--SR or -COOR', or (i
l An expression in which both G and σ are an alkyl group having 1 to 4 carbon atoms. ] In the production of a compound represented by. tal A compound of the following formula ■: (wherein, X is the same as the definition of formula 1) is added to the following formula layer: (identical) in the presence of a base, or tb) a compound of the following formula ■: (wherein X is the same as the definition of formula I and °D represents an elimination radical), React the compound of formula m: R 凰cloud HN-Q-Z (In) (in which R1, Q and Z are the same as the definitions of formula ゛■), or Ic) the following formula v: ゛1 paste ) (In the formula, X, Q and Z are the same as the definition of Bu I, T represents a hydrogen atom or a nitro group) is reacted with an anhydride or an acid chloride, and if T is a hydrogen atom, The obtained reaction product is nitrated to obtain a compound vA in which R1 is a fulkylcarbonyl group having 1 to 4 carbon atoms, or ld) The following formula (1): (wherein, X is A compound of the following formula 1 -Q-Z / (5!c, where R1, Q and Z are the same as the definition of formula I /11
7R) -) is reacted at high temperature in the presence of a base to form the following formula ■
: I (wherein % (same as defined above) with a corresponding alkylating reagent to obtain a compound in which RJ in formula I has 1 to 4 carbon atoms, or to obtain a compound in which Z in formula I is a carboxyl group from tfl pfrWK itself. A manufacturing method in which the compound is converted into the corresponding carboxylic acid derivative by a known method. a nitroso group or a C1 -C4 alkyl group, a C2 -C4 alkenyl group, a C1 -C4 alkylcarbonyl group or a C2 -C4 alkenylcarbonyl group; represents a group unsubstituted or substituted with one or more halogen atoms; Alkyl group of 4 1, t, t, <
it 2 m] @ff1t, ri # exchange iAS ES GS
υ, and M′ are the bonds between the two monoatomic atoms to which they are bonded; A, E, G, L, and M are hydrogen atoms or A, E, G, One or two of L and M are also -0R3;-8R'';-
COOR'; charcoal, -8R' or -CUOR'; or -OR', -8R' or -CUOR'
C 1 -C 4 alkyl group substituted by (
RζR", R', R'. R6 and R1 represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; a. b, c and d represent 0 or 1; or &
iR1 and G together destroy trimethylene, and a.
b, c and d represent a straight-chain or branched aliphatic radical having 1 to 5 carbon atoms; and Z represents a group: -0000M♀, -cooR', -C
O8R'. , -CONR' 甑 -〇〇RII or 〇f'll
(In the formula, He is a cation, and R is a hydrogen atom;) ~ #2s unsubstituted or substituted by a rogen atom, cyano, or an alkoxy group having 1 to 4 carbon atoms, number of atoms 1
an alkyl group having 2 to 8 carbon atoms; or an alkynyl group having 3 to 8 carbon atoms, R11 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an alkyl group having 3 to 6 carbon atoms; Noshi,
R10 is a hydrogen atom; an amino group; a hydroxyl group; a C1-C4 alkyl group unsubstituted or substituted with a C1-C4 alkoxy group; or a C2-C4 alkynyl group; group, an alkoxy group having 1 to 4 carbon atoms; %L< is a dichloroalkylaminocarbonyl group having 3 to 6 carbon atoms, and R11 is a hydrogen atom; or an alkoxy group having 1 to 4 carbon atoms, and A substituted or substituted 4-alkyl group having 1 to 4 atoms (representing a 4-alkyl group having 1 to 4 atoms), provided that in the compound, at the same time K R' is a hydrogen atom, and a, b
, when c and d are O, 1llG is -OR";-
COOR'; or -OR'', an alkyl group having 1 to 4 carbon atoms substituted with -8R or -〇〇R', or fill G and G both represent an alkynyl group having 1 to 4 carbon atoms v ] A herbicide containing as an active ingredient at least 1t!J of the compound represented by the formula!.
25. The herbicide according to claim 24, which contains S, 1 to 999 parts by weight of additives, and 1 to 25 parts by weight of surfactants. (4) 0.1 to 95 mt% of the compound represented by formula I,
Additives 5 to 9t8') R and surfactant α
26. The herbicide according to claim 25, containing from 1 to 25 parts by weight. (In the formula 2, R1 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms; Re and R" represent 1 hydrogen atom.)
The herbicide according to claim 24, which contains a compound as an active ingredient. (e) Methyl he[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenyl2
The herbicide according to claim 27, which contains -aminopropionate as an active ingredient. Methyl He [2-nitro-5-(2-chloro-4
-1-17fluorometherphenoxy)phenyl]-4
The herbicide according to claim 27, which contains -amino-n-phthalate as an active ingredient. Button Isopropyl to [2-nitro-5-(2-chloro-4-trifluoromethylphenoxy) phenyl-3-amino, the herbicide listed in Claims\Claim 27-2 containing globionate as an active ingredient . C11) The herbicide according to claim 27, which contains ether h-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenyl-3-aminoglobionate as one active ingredient. . □□□ The herbicide according to claim 27, which contains he[2-nitro-5-(2-chloro-4-trifluorometherphenoxy)phenyl]-5-7 minoprionic acid as an active ingredient. . @ To-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenyl]-4-amine 7n
-Claim 427 containing butyric acid as an active ingredient
Herbicides listed in section. to C114S-C-(2-nido-5-(2-ri1:1
(4-trifluoromethylphenoxy)phenyl)-
The herbicide according to claim 27, which contains aminoco-propionamide as an active ingredient. 25. The herbicide according to claim 24, which comprises a homogeneous mixture of one or more of the above-mentioned active ingredients, a solid or liquid carrier, and optionally a surfactant. (7) The herbicidal efficacy of the compound of formula I or the composition containing the compound is applied to the crop or the area where it is planted during the cultivation of useful plants to control the growth of undesirable plants. The herbicide according to claim 24. (9) The herbicidal efficacy I of the composition containing the compound of formula I or the @ compound is applied during the cultivation of cereals, wheat, barley and rice to the crops or the place where they are planted, and to control dicotyledonous weeds. 25. The herbicide according to claim 24, which controls the herbicide before germination. @ A herbicidally effective amount of a compound of formula I or a composition containing said compound is administered during the cultivation of cereals, wheat, barley and rice.
Claim 24i for controlling dicotyledonous weeds after their germination by applying to the crop or the place where it is planted.
Herbicides listed. (7) The following formula f: R凰■ [In the formula, X represents a hydrogen atom, a chlorine atom, a fluorine atom, or a bromine atom, and R1 is a hydrogen atom, a nitroso group, or an alkyl group having 1 to 4 carbon atoms, An alkenyl group having 2 to 4 carbon atoms, an alkylcarbonyl group having 1 to 4 carbon atoms, or an alkenylcarbonyl group having 2 to 4 atoms, each consisting of 1al or more halogen atoms. represents an unsubstituted or substituted group, and Q represents a group of the following formula: Substituent A: E; G: υ and M' represent the bond between the two leg atoms to which it is attached; A,
E, G, L and M are water yLJjA child or A
, E, G, L and 1 fm or 2 of M are also 10R2; -8R';-CUOR'; 2 or 10R', -
8R' or -COOR'-substituted alkyl group having 1 to 4 carbon atoms (R'', R', R',
R6, R' and R7 are hydrogen atoms or carbon atoms'
#! i1 to 4 alkyl group); a, b
, c and d represent 0 or 1; or R1
and G together represent a trimethylene bridge, and a, b
, C and d represent 0;
and ztt, a: -coo"pa'l, -eo
oRl, -cosPe. -CONR"R product Q, -CORII or 1;j -
CN (In the formula, M stands for a cation, and H stands for a hydrogen atom:)
- an alkyl group having 1 to 8 carbon atoms which is unsubstituted or substituted with a rogone atom, cyano or an alkoxy group having 1 to 4 carbon atoms; an alkenyl group having 2 to 8 carbon atoms; or an alkenyl group having 2 to 8 carbon atoms; R9 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a cycloalkyl group having 3 to 6 carbon atoms; R10 is a water 3I!\ atom; a) group; a hydroxyl group;
a C1-C4 alkyl group unsubstituted or substituted with a C1-C4 alkoxy group; or a C2-C4 alkynyl group; a C1-C4 alkyl group;
to 4 alkoxy group or a cycloalkylaminocarbonyl group having 5 to 6 carbon atoms, and R1
1 represents a hydrogen atom; or an alkyl group having 1 to 4 carbon atoms which is unsubstituted or substituted with an alkoxy group having 1 to 4 carbon atoms; however, in the compound, at the same time K R' is a hydrogen atom, alI) IC and d
When is 0, (1) G is -OR";-COUR';
or -0R--8R' or -cooRt
an alkyl group having 1 to 4 carbon atoms, or +ill where G and G' both represent an alkyl group having 1 to 4 carbon atoms; ] A composition for drying or defoliating cotton or potato plants, which contains a compound represented by the following as an active ingredient. Compound 01 to 99N Keigamo represented by formula 1, additive 1 to ? ? 39. The composition of claim 39, comprising a surfactant, 9:II, and a surfactant. Compound α1f being played with by Lord Take■! Ishi 95. Claim 3 containing IE amount S, fA additive 5 to 99.8 weight range and surfactant α, 1 to 25 Nt%
Composition according to item 9. (iv) In the formula I, a compound in which X and R1 are hydrogen atoms, Q is ethylene or ゛ is a trimethylene bridge, and Z is a methoxycarbonyl group or an allyloxycarbonyl group. 5
The composition described in 9m. Methyl He [2-nitro-5-(2-chloro-4
-trifluoromethylphenoxy)phenyl)-4-
43. The composition according to claim 42, which contains the composition as a component targeting 7 min. ■ Methyl to-[2-nitro-5-(2-chloro-4
-trifluoromethylphenoxy)phenyl]-3-aminopropionate as an active ingredient. - Allyl I'V-(2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenyl]-5
-A composition according to claim 42, containing aminopropionate as an active ingredient. (2) One or more of the active ingredients and a solid or liquid carrier, optionally a surfactant, are uniformly mixed. The herbicidal effect of the compound of formula i or a composition containing the compound is applied to cotton or potatoes *'91JK and dried or defoliated Claim No. 59Mk
Composition listed in No. 2. - the compound of formula 1 or the group f containing the compound! t@
Effective for weeding! Ik is applied to cotton or potato plants before harvesting and allowed to dry or defoliate. ! fr
f The composition odor described in claim 69 @