JPS59175487A - N-pyridylpyrazole derivative useful as herbicide - Google Patents

Abstract

(57) [Summary] 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 N-pyridylpyrazole derivatives, compositions containing them and their use as herbicides.

The present invention is based on the general formula I defined herein [wherein R1 is (1) a hydrogen atom, (n) R'C(=O)- group (where R4 is a hydrogen atom, 1 to 7 straight-chain or branched alkyl groups having carbon atoms; straight-chain or branched alkoxy groups having 1 to 4 carbon atoms; straight-chain or branched alkoxy groups having 3 or 4 carbon atoms; represents an alkenyloxy group; alkyl and alkoxy groups within the definition of u4 are unsubstituted or straight-chain or branched alkoxy groups having 1 to 4 carbon atoms; (or R4 is unsubstituted or substituted by a methyl or ethyl group). represents a cycloalkyl group having ~6 carbon atoms,
or R4 represents a phenoxy group), (Il+) group R5 (here R5 is 1 to 8, preferably 1
R' represents a straight-chain or branched alkyl group having ~4 carbon atoms or a straight-chain or branched alkenyl or alkynyl group having 2 to 8, preferably 2 to 4 carbon atoms; The alkyl, alkenyl, and alkynyl groups represented by 5 may be unsubstituted or cyano, hydroxy, straight-chain or branched alkoxy, carboxy, or carboxy groups having 1 to 6 carbon atoms. a straight-chain or branched alkoxycarbonyl group, an aminocarbonyl group having carbon atoms of and when the aminocarbonyl group is substituted with two alkyl groups, these may be the same or different (or two to
If one or two straight chains with 8 carbon atoms...
, may be substituted by a branched alkenyl or alkynyl group (and if the aminocarbonyl group is substituted with two alkenyl or alkynyl groups, these may be the same or different), an alkoxyaminocarbonyl group having 1 to 8 carbon atoms and which may be straight or branched; the alkane moiety is 1 to 8;
an alkanesulfonamidocarbonyl group having up to two carbon atoms and which may be straight-chain or branched; A saturated nitrogen-containing multicyclic ring having 3 to 7 atoms in the ring containing a terror atom and bonded via a nitrogen atom to the -C(-0)- group of the 10(-0) He1 group. ) or substituted by one or more halogen atoms (e.g. chlorine atoms), or B5 is unsubstituted or one or more straight or branched chains having 1 to 4 carbon atoms 3-6 substituted with a lower alkyl group (e.g. methyl or ethyl group)
Indicates a Schifftetraalkyl group having 4 carbon atoms, R2 is a hydrogen atom when (+)R" is a hydrogen atom, (II) R" is a R'C(-0)- group (Here, R4 has the above meaning) is a hydrogen atom or R'Q
, (-〇)- group (where R4 has the above meaning), (iii) if R1 represents a group R5 (where R5 has the above meaning), a hydrogen atom or within the definition of R5 above; represents a certain group, or R1 and R2 together represent -
Co(CRaRb)-Co-(ko,:, where Ra and Rb may be the same or different (, each represents a hydrogen atom or a straight-chain or branched alkyl group having 1 to 4 carbon atoms; , m represents 2 or 3), or R1 and R2 together with the nitrogen atom to which they are bonded represent a group of general formula H as defined herein, where BClRCl, E”, Rf, Rg and R
h may be the same or different (, each represents a hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms, n represents 0.1 or 2, n represents 1 or 2 In the case of representing the group of the above general formula (■), the part = [(R
o) C(-Rd))- and -[(Ro-)C(-Rc
l)) 2-(7) R0 Oyohi Rd Ha Same Teari-71m
may also be different (or R1 has 1 to 4 alkyl moieties)
represents an alkylthio group having R1 carbon atoms and which may be straight or branched, and B2 represents a hydrogen atom, or R1
and R2 together with the nitrogen atom to which they are bonded represent a group of general formula XXXII as defined herein,
where Hp is substituted by a straight-chain or branched alkoxy group having 1 to 4 carbon atoms or 1 or 2 straight-chain or branched alkyl groups each having 1 to 4 carbon atoms. When the amine group is substituted with two alkyl groups, these may be the same or different, and Rq is a hydrogen atom or 1 to 4
a straight-chain or branched alkyl group having 5 carbon atoms, R3 represents a general group 2 as defined herein, and B6 represents a chlorine atom]. Pyrazole derivatives, and when R5 represents an alkyl, alkenyl or alkynyl group substituted by a carboxy group, their salts with agriculturally acceptable bases are provided, which have beneficial herbicidal properties.

R1 and R2 each represent a group R4ct(-〇)-,
Here, when R4 has the above meaning, the R'C(-
It is to be understood that the 0)- groups may be the same or different.

Furthermore, -(CB,B)□- is an unsubstituted ethylene or propylene group, or one of the straight-chain or branched alkyl groups in which one or more of the carbon atoms has 1 to 4 carbon atoms. or 2-substituted ethylene or propylene groups.

Also, unless otherwise specified, the term "halogen" should be understood to mean halogen, bromine or iodine.

Furthermore, when R1 and R2 each represent a radical R5, where R5 has the abovementioned meaning, it is to be understood that said R5 groups may be the same or different.

The term "salts with agriculturally acceptable bases" means salts in which the cation is known and accepted in the art for producing salts of agriculturally or horticulturally insecticidal active acids.

Preferably these salts are water soluble. Suitable salts with bases include alkali metal (e.g. sodium and potassium), alkaline earth metal (e.g. calcium and magnesium), ammonium and amine (e.g. jetanolamine, triethanolamine, octylamine, morpholine and dioctylmethylamine) salts. includes. In this specification, when the compound of the general formula (2) is explained, it should be understood that the explanation is intended to include the salt of the compound of the general formula (2) with an agriculturally acceptable base, as necessary.

The following compounds of general formula (2) are of particular interest as herbicides: 2M and B/lfi compounds 418
12 1 5-amino-4-cyano-1-(3-rip
5-trifluorotatylpyrid-2-yl)pyrazole 42527 2 1- (3-chloro-5-trifluoromethylpyrid-2-yl) -4-cyano-5-diacetylaminopyrazole 42528 3 5-acetamide -1-(3-chloro-5-trifluoromethylpyrid-2-yl)-4-cyanopyrazole 42628 4 1- (3-chloroA'-5-)trifluoromethylpyrid-2-yl) - 4-cyano-5-ethylaminopyrazole 42646 s z -(3-chloro-5-trifluoromethylpyrid-2-yl) -4-cyano-5-methoxymethyleneaminopyrazole 6l-(3-chloro-5 -trifluoromethylpyrid-2-yl) -4-cyano-5-propionamide pyrazole 7 1-(3-chloro-5-trifluoromethylpyrid-2-yl) -4-cyano-5-dichloroaceta Midopyrazole 8l-(3-chloro-5-trifluoromethylpyrid-2-yl) -4-cyano-5-succinimidopyrazole 42697 9 1-(3-chloro-5-trifluoromethylpyrid-2-yl) -4-cyano-5-di(phenoxycarbonyl)aminopyrazole 42699 10 1-(3-chloro-5-trifluoromethylpyrid-2-yl) -4-cyano-5-impropoxycarbonylaminovirazole 42698 11 1-(3-chloro-5-trifluoromethylpyrid-2-yl)-4-cyano-5-methoxycarbonylaminopyrazole 42683 12 5-(3-chloro-2-methylpropionamide)-1-( 3-chloro-5-trifluoromethylpyrid-2-yl)-4- 7anopyrazole 42684 13 1-(3-chloro-5-trifluoromethylpyrid-2-yl)-4-cyano-5-( 3-Methyl-2-oxo-azetidin-1-yl)pyrazole 42700 14 1-(3-chloro-5-trifluoromethylpyrid-2-yl)-4-cyano-5-(2-probenyloxy carbonylamino) Pyrazole 15 1-(3-chloro-5-trifluoromethylpyrid-2-yl)-4-cyano-5-pentanamide pyrazole.

According to a feature of the invention, a small number (at least one N
- A method for controlling the growth of weeds (i.e., undesirable vegetation) in a habitat is provided, the method comprising applying a herbicidally effective amount of a pyridyl pyrazole derivative to the habitat. For this purpose, N-pyridylpyrazole derivatives are
They are generally used in the form of herbicidal compositions (ie, in combination with diluents or carriers suitable for use in herbicidal compositions), such as those described below.

The compounds of general formula I exhibit herbicidal activity against dicotyledonous (ie, broadleaf) and monocotyledonous (eg, grasses) weeds upon pre- and/or post-emergence application.

The term "pre-emergent application" means application to soil in which weed seeds or seedlings are present before the appearance of weeds on the surface of this soil. The term "post-emergent application" means application to the air or exposed parts of weeds that have emerged on the surface of the soil. For example, compounds of general formula
Aethusa cynapium), Ab
utilontheophrasti), Amaranthus retroflexus
, Am5inckia
intermedia), Ruri no Kobe (Ana
Gallis arvensis), Anthemis arvensis, Atriplex patula, Bidens pilosa, Brassica nigra
, shepherd's purse (Capsella bursa -pasto)
ris), Cbenopodiumalt
um ), Chrysanthemum segetum (chrysa
nt, hemum seget, um), Cirsium a, rveise, Datura
stramonium), Desmo
diurr+ tortuosum), Emex Australia (Emex australia)
, Euphorbia heliosc
opia), 7 Maria officinalis (Fumar)
ia officinalis), Chishimaeopsou (Ga1eops), Yaemugura (Gal
ium aparine), geranium
8ana communis), Matricaria
Inodora (Matricaria anal interlock), Monochoria nokuginaris (Monochoria va, I Koshu i5), ':/':6 Le Roeas (force 1 particle rh, oeas), Fuiz8 squirrel fist Longihoria (P
hvsalis rice cake), spatula, t Oha: I
Polygonum spp, Polygonum lapath
ifolium), Niwayanagi (Urie fourμpress avi
culare), Sono9ka (Paphanus ra)
phanistrum), Rotala 0 insica (Rot.
aLa 1ndica), Ezonogishikishi (Seisobutusifolius), Sabonunwu (7vac
caria), Scandix pecten-Vθneris
), 5enecio vulgari
s), Sesno Kunia Florida (5esbania
florida) s American Kingon” power (and%
Sirene 7 A/A (Si1μYa)
lb & ), Sinapis alpensis (Sinapis)
arvensis), Solanum
μm Futatsuki), Taiwan Hachijouna (5onchus
arven, sis).

Giant clover (7 arvensis), /z kobe (5tellaria meclia), Gunnoku arvense (Th1as Yui arvense), Noumabishi (Trifall1sterrestria), Northern nettle (Urticaurens) , Veronica Hederif
olia), (l heE' Nika-Persica (V
'Viola persica), 'Viola arvensis' and Xantium St.
rumariurq), as well as grass weeds such as Alopecurus myosuroides.
M osuroides ), Apera ■Venti Yamayuji Venti ) and Acrosteis Stronifuera (AgrOstiSstolo )
nifera), oat (Avena fatu)
a), Ahenaru Tobisiana
tciana), Pukuchibuno■〃-species (Bra
chiaria mutual ■ giant), Bromus sterilis (B
romus 5terilis).

Cynodon, dactylon, 73ana ui na lis,
hal-epense) and Carex weeds,
It is possible to limit the length of the analogy by one kaya.

The amount of compound of general formula I used will vary depending on the nature of the weeds, the composition used, the time of application, the season and soil conditions, and (when used to control weed growth in crop growing areas) the nature of the crop. When applied to crop growing areas, the application rate should be sufficient to control weed growth without causing substantial permanent damage to the crop. Generally, taking these factors into account, o per hectare
, o 1kli+-1okg of active substance gives good results. However, it should be understood that higher or lower application rates may also be used depending on the particular weed control problem encountered.

Compounds of general formula I can be used to selectively suppress the growth of weeds, e.g. the growth of plants of the above-mentioned types can be inhibited directionally or non-directionally by pre- or post-emergence application, e.g. By direct or non-directional spraying, crops such as cereals (e.g. wheat, barley, oats, corn, rice, soybeans and other legumes, peas, alfalfa, cotton, peanuts, flax, onions, carrots, cabbage, oilseed, sunflowers) can be sprayed. Weed control is applied to areas used or to be used for growing (e.g., sugar beets) and areas of weed infestation, including permanent and seeded pastures, before or after seeding the crop, or before or after crop emergence. I feel anxious about doing it. For example, to selectively suppress weeds in areas of weed infestation that have been or should be used to grow crops of the types described above,
0.01-4.0 kg per hectare, preferably 0
．． An application rate of active substance of 9 to 1 to 2.0 is particularly suitable.

More specifically, compounds of general formula ■ can be used to selectively suppress the growth of broadleaf weeds, for example, before the emergence of both crops and weeds on areas used to grow cereal crops. Or later by non-directional spraying, the growth of broad-leaved weeds of the types described above can be inhibited by pre- or more preferably post-emergent application.

For this purpose, i.e. to selectively control broadleaf weeds by pre- or post-emergence application to areas used for growing cereal crops, 0.01 to
4.0 kg, preferably 0.0 kg. Application rates of active substance of O1-2, okg are particularly suitable.

Furthermore, the compounds of general formula I can be used by pre- or post-emergence application in established orchards and other tree-growing areas, such as forests, woodlands and parks, as well as on large farms, such as sugar cane, palm and rubber plantations. The growth of weeds, especially those mentioned above, can be suppressed. For this purpose, 0.25 per hectare before or after planting crossbars or plants, either directionally or non-directionally (e.g. by directional or non-directional spraying) on the weeds or on the soil where weeds are expected to appear. ~10.0kg,
Preferably 1.0 to 4. It can be applied at an application rate of 0 kg of active substance.

Compounds of general formula I can also be used to control the growth of weeds, particularly the weeds mentioned above, in areas where crops are not grown, but where weed control is desired. Examples of areas that do not grow this type of crop are airports,
Includes industrial sites, railroads, roadsides, riverbeds, industrial or other waterways, woodlands and fallow lands, or uncultivated land where it is desirable to suppress the growth of weeds to prevent the occurrence of fires. When used for purposes of this type, where an overall herbicidal effect is often not desired, the active compounds are generally applied at higher application rates than those used in the crop growing areas mentioned above. The exact amount used depends on the nature of the vegetation to be treated and the desired effect. directionally or non-directionally (e.g. by directional or non-directional spraying)
2.0 to 10.0 tons per hectare, preferably 4.
0) 91~to', Ok+? If used before or after emergence, preferably before emergence, at an application rate of active substance of
Particularly suitable for this purpose.

When used to control the growth of weeds by pre-emergent application, the compounds of general formula I can also be incorporated into the soil where weeds are expected to appear.

By post-emergence application using compounds of general formula I.

That is, when weed growth is inhibited by application to the air or exposed parts of emerging weeds, it is understood that compounds of general formula I generally come into contact with soil and exert pre-emergence inhibition on subsequent weed germination in the soil. be done.

Applications of compounds of general formula I can be repeated as necessary, especially if long-term weed control is required.

According to another feature of the invention, there is provided a composition suitable for curtaining applications, which composition comprises combining one or more N-pyridylpyrazole derivatives of general formula I with one or more herbicidal A suitable acceptable diluent or carrier (i.e., a type of diluent or carrier generally recognized in the art as suitable for use in herbicidal compositions and compatible with compounds of general formula I). It is preferably contained homogeneously dispersed therein.

The term "homogeneous dispersion" is also used to encompass compositions in which the compound of general formula 1 is dissolved in other ingredients. The term "herbicidal composition" is used broadly to include not only ready-made compositions for use as herbicides (but also concentrates which must be diluted before use). Preferably, these compositions The product has a general formula I with a weight ratio of 0.05 to 90
Contains one or more of the following compounds.

Herbicidal compositions include a diluent or carrier and a surfactant (
eg wetting agents, dispersing agents or emulsifying agents). The surfactants that can be present in the herbicidal composition of the present invention can be ionic or non-ionic, such as sulfolisylates (5ulpho
hicinoleates), quaternary ammonium derivatives, compounds based on condensates of ethylene oxide with alkyl and polyarylphenols (e.g. nonyl- or octylphenols), or soluble compounds by etherification of free hydroxy groups by condensation with ethylene oxide. Carboxylic acid esters of sorbitol anhydride, such as dinonyl- and dioctyl-sodium sulfonosuccinates, alkali metal and alkaline earth metal salts of sulfuric acid esters and sulfonic acids, as well as sodium and calcium lignosuccinates, Includes alkali metal and alkaline earth metal salts of high molecular weight sulfonic acid salts such as sulfonates, sodium and calcium alkylbenzene sulfonates.

Suitably, the herbicidal composition according to the invention may contain up to xo, for example from 0.05 to % of a surfactant,
If desired, the herbicidal compositions of the invention can contain higher proportions of surfactant in the liquid emulsifiable suspension concentrate, for example up to 15% of the surfactant in the aqueous liquid. Can be included in concentrates.

Examples of suitable solid diluents or carriers are aluminum silicates, talc, calcined magnesia, diatomaceous earth, tricalcium phosphate, powdered cork, adsorbent carbon blacks, and clays such as kaolin and bentonite. Solid compositions (which may be in the form of powders, granules or wettable powders) are preferably prepared by grinding a compound of general formula (1) with a solid diluent or by adding a volatile solvent to a solid diluent or carrier. It is prepared by impregnating a solution of a compound of general formula I in a powder, evaporating the solvent and optionally grinding the product to obtain a powder.

Granular compositions can be prepared by adsorbing a compound of general formula (I) (dissolved in a suitable solvent, which may be volatile if desired), onto a solid particulate diluent or carrier and, if desired, evaporating the solvent; It can be manufactured by granulating the powdered composition obtained as described above. Solid herbicidal compositions, especially wettable powders and granules,
If solid, it may contain wetting or dispersing agents (eg of the type mentioned above) which can also act as diluents or carriers.

The liquid compositions of the invention may be in the form of aqueous, organic or aqueous-organic solutions, suspensions and emulsions, which may contain surfactants. Suitable liquid diluents for inclusion in liquid compositions include water, glycols, tetrahydrofurfuryl alcohol, acetophenone, cyclohexanone, isophorone, toluene, xylene, mineral, animal and vegetable oils, and light aromatic and naphthenic fractions of petroleum, and Mixtures of these diluents are included. Surfactants that may be present in liquid compositions may be of ionic or non-ionic type (eg of the types described above) and, when liquid, may also act as diluents or carriers.

Liquid compositions as wettable powders, dispersible granules and concentrates may be diluted with water or other suitable diluents such as mineral or vegetable oils, especially in the case of liquid concentrates where the diluent or carrier is an oil. −(, g'<::a
A similar composition can be obtained.

If desired, liquid compositions of compounds of general formula I can be used as self-emulsifying concentrates containing the active substance dissolved in an emulsifier or in a solution containing an emulsifier compatible with the active substance. The simple addition of water to such concentrates provides ready-to-use compositions.

Liquid concentrates where the diluent or carrier is an oil can be used without further dilution (using electrostatic spraying techniques).

Furthermore, the herbicidal compositions of the present invention may optionally contain customary adjuvants such as adhesives, protective colloids, thickeners, penetrants, stabilizers, sequestrants, anticaking agents, colorants and corrosion inhibitors. It can contain. These adjuvants can also act as carriers or diluents.

A preferred herbicidal composition of the present invention comprises one or more compounds of the general formula (1) of 10 to 70 parts, a surfactant of 2 to 10 parts, a thickener of 0.1 to sw/v4, and 15 to 70 parts of a surfactant. ~87.9
Aqueous suspension concentrate consisting of volumetric water; 10-90 W
/W one or more compounds of the general formula ■ and 2
~10 w/w 4 surfactants and 10-88 w/w
'It's a water-compatible powder with a solid diluent or carrier; 5-50%, e.g. 10-30 w7v%
one or more compounds of general formula I of 5 to 25
w/v % surfactant and 25~! A liquid water-soluble concentrate consisting of 11.1%, e.g. 45 to 85 volume, of a water-miscible solvent, e.g. dimethylformamide, or a mixture of water-miscible solvents and water; general formula of lθ to 70 w/v range. one or more compounds of I and 5 to 15 w
/v % surfactant, 0.1 to 5 w/v % thickener and 10 to 84.9 parts by volume organic solvent; 1 to 90 parts, for example 2 ~10 w/w
4, one or more compounds of the general formula (2) and 0.4.
particle size 11 consisting of a surfactant of 5-7%, e.g. 0.5-2 w/w, and a particulate carrier of 3-98.5%, e.g. 88-97.5 w/w; 05～
90 w/v %, preferably 1 to 60 w/v'l of one or more compounds of general formula I and α01 to lO
w/vJ preferably 1-10 w/v 9J of surfactant and 9.99 to 99.94, preferably 39 to 98.99
It is an emulsifiable concentrate consisting of a volumetric organic solvent.

The herbicidal composition of the present invention further comprises a compound of general formula I, x
1M or more of other insecticidal active compounds and, if desired, together with one or more suitable insecticidal-acceptable diluents or carriers, surfactants and conventional adjuvants as described above, preferably homogeneously dispersed. be able to. Examples of other insecticidal active compounds that can be included in or used in conjunction with the herbicidal compositions of the invention include herbicides such as azichlor, for example to increase the range of weed species to be controlled. 2
-Chloro-2', 6'-diethyl-N-(methoxymethyl)-acetanilido], aslam[methyl (4
-aminebenzenesulfonyl)-carbamate], alloxydim Na [λ-[1-allyloxy-aminobutylidene)-5,5-dimethyl-4-methoxycarbonylcyclohexane-1,3-dione sodium salt], atrazine [2- Chloro/I/-4-ethylamino-6-inpropylamino-1,3,5-) 1,1 azine],
Parpan [4-chlorbudo-2-ynyl N-(3-chlorophenyl)carbamate], Benzoylprog-ethyl [N-benzoyl-N-(3,4-dichlorophenyl-2-aminopropionate ethyl)], Bromoxynil [3 ,5-dibromo-4-hydroxybenzonitrile]
, butachlor [N-(butoxymethyl)-2-chloro-
2', 6'-ethylacetanilide], butyrate [
S-ethyl N, N-diisobutyl nithiocarbamate]
, carbetamide CD -N-ethyl-2-(phenylcarbamoxyloxy)propionamide], chlorfenprobu-methyl [methyl 2-chloro-3-(4-70ruphenyl)furopionate], chlorpropham [N −
(3-chlorophenyl)isopropyl carbamate],
Chlortoluron [N'-(3-chloro-4-methylphenyl)-N,N-dimethylurea], cyanazine [2-chloro-4-(1-cyano-1-methylethylamino)-
6-nitylamino-1,3.5-)riazine], cycloate [N'-cyclohexyl-N-ethyl-8-:r
-thyl(thiocarbamate)], 2.4-D[2,4-
dichlorophenoxyacetic acid], daravone [2,2-dichloropropionic acid], 2,4-DBC4-(2,4-dichlorophenoxy)butyric acid], desmedifam [3-(ethoxycarbonylamino)phenyl N-phenyl- carbamate], sialate [8-2,3-dichloroallyl-
N,N-diisopropyl (thiocarbamate)], dicamba [3,6-dichloro-2-methoxybenzoic acid], dichloroprop [[±)-2-(2;4-dichlorophenoxy)propionic acid], difenzoquat [1 ,2-dimethyl-3,5-diphenyl-pyrazolium salt], dimefuron[4-[2-chloro-4-(3,3-dimethylureido)phenyl]-2-t-butyl-1,3,4-oxa diazolin-5-one], dinitramine (Nl,
Ni-diethyl-2,6-sinitro 4-) I
J fluoromethyl-m-phenylenediamine], silaron [N'-(3,4-dichlorophenyl)-N,N-dimethylurea], EPTC [S-ethyl N, N-dipropyl (thiocarbame)) ethofumesate [ 2-ethoxy-2,3-dihydro-3,3-dimethylbenzofuran-5-yl-methylsulfonate], flamprobuinpropyl [(t)-2-(N-benzoyl-3-chloro-4-fluoroanilino) ) Isopropyl propionate]
, flampropmethyl [(branch)-2-(N-benzo-3
-ChloA/-4-fluoroanilino)-10 methyl pionate], Fluometuron [N'-(3-trifluoromethylphenyl)-N,N-dimethylurea], Ioxynyl [4-hydroxy-3,5- diiodobenzonitrile], Improblon (N'-(4-impropylphenyl)-N, N-dimethylurea), Linuron [N-(
3,4-dichlorophenyl-N-methoxy-N-methylurea], MCPA [4-chloro-2-methylphenoxyacetic acid], McpB [-(4-chloro-2-methylphenoxy)butyric acid], Mecoprob [( )-2-(4-chloro-2-methylphenoxy)pyropionic acid], metamidrone [4-amino-3-methyl-6-phenyl-1,2,
4-triazin-5(4H)-one], metabenzthiazuron [N-(benzothiazol-2-yl)-N,
N'-dimethylurea], metribudin [4-amino-6-t-butyl-3-(methylthio)-1,2,4-
triazin-5-(4H)-one], molinate [S-
Ethyl N,N-hexamethylene (thiocarbame)
:], oxacycin [3-(2,4-dichloro-5-
impropoxyphenyl)-s-t, -butyl-1,3
, 4-oxadiazolin-2-one], baraquat [1
, 1'-dimethyl-4,4'-bipyridylium salt], peplate CB-propyl N-butyl-N-ethyl (thiocarbamate)], phenmedipham (:N-(3-
3-(methoxycarbonylamino)phenyl)carbamate], promethrin [4,6-pisisopropylamino-2-methylthio-1,3,5-)riazine], propachlor [2-chloro-N-isopropylacetanilide] ], Propanyl (N-(3,4-dichlorophenyl)-propionamide), Propham [N
- phenylcarbamate Improvir], pyrazole [
5-amino-4-chloro-2-phenylpyridazine-3
(2H)-one], simazine [2-chloro-4,6-pisethylamino-1,3.5-)riazine), TCA[
) dichloroacetic acid], thiopencarb [8-(4-chlorobenzyl) -N + 1'T-die2thylthiolcarbamate], triarene) [8-2, 3, 3-)
dichlorallyl N,N-diisopropyl (thiocarbamate)] and trifluralin [2,6-sinitro N,N-dimethrin; and fungicides such as 2,6-
Dimethyl-4-tridecyl-morpholine, N-(1-butyl-carbamoyl-benzimidazol-2-yl)
Methyl carbamate, 1,2-bis-(3-methoxycarbonyl-2-thioureido)benzene, isopropyl-1-carbamoyl-3-(3,5-dichlorophenyl)hydantoin and 1-(4-chlorophenoxy)-
3,3-dimethyl-1-(1,2,4-triazole-
1-yl)-butan-2-one. Other biologically active substances that may be included in or used in conjunction with the herbicidal compositions of the present invention include plant growth regulators such as succinamic acid, (2-chloroethyl)trimethylammonium chloride and 2-chloroethane- phosphonic acids; or fertilizers, such as nitrogen, potassium and phosphorus and trace elements known to be essential for plant life;
For example, fertilizers containing iron, magnesium, zinc, manganese, cobalt, and copper.

Insecticidal active compounds and other biologically active substances that can be contained in or used together with the herbicidal composition of the present invention, such as the acids mentioned above, can be added as necessary to conventional derivatives. , for example as alkali metal and amine salts and esters.

According to another feature of the invention, there is provided an article of manufacture consisting of at least one N-pyridylpyrazole derivative of general formula I, or preferably a herbicidal composition as described above, which preferably has to be diluted before use. N- of the general formula ■
At least one pyridyl pyrazole derivative has the general formula ■
a herbicidal concentrate comprising a herbicidal concentrate in a container for said derivatives and how to use a conductor of the general formula An article of manufacture is provided comprising instructions for inhibiting weed growth. These containers are generally of the type customary for storing chemicals that are solid at room temperature and in particular herbicidal compositions as concentrates, such as metal cans and drums that can be internally lacquered. Cans and drums of plastic material, bottles of glass and plastic material, and also boxes or bags made of, for example, cardboard, plastic material and metal if the contents of the container are solid, for example granular herbicidal compositions. It can be done. These containers generally contain an amount of N-pyridyl sufficient to treat at least one acre of land to control the growth of weeds present thereon, but not to exceed an amount convenient for conventional handling methods. The volume is sufficient to contain the pyrazole derivative or the herbicidal composition. The instructions may be physically attached to the container, for example printed directly on it, or printed on a label or tag affixed thereto. These instructions generally indicate that the contents of the container, after dilution if necessary, are to be used for the abovementioned purpose at an application rate of active substance of from 0.01 to xokH per hectare for controlling the growth of weeds.

(below F margin) The following major examples illustrate 19 herbicidal compositions of the present invention.

Tora Shi? I11 A hydratable powder was prepared from the following ingredients: 5-amine-1-(3-chloro-5-trifluoromethylpyrid-2-yl)-4-cyanopyrazole
50 w/w% Eteran BCP
(KM per mole of 9 moles of eterenokephenol oxide)
Y nonylphenol/I oxyethylene condensate)
5 w/W% Aerosil (tll, thin cypress size of two-dimensional silicon: g) 5 w/w% Celite 1) In order to create powdered wood, ethylane BCP is absorbed onto Aeroflu, mixed with other ingredients, and ground in a mill to produce aqueous phase t4E'6) powder. -C1 This hydratable powder is dispersed with water to produce 300 tI:P of hydrating powder I K7 per hectare of J4 liquid.
The diversion side of the sweat is done by Yaemugura (Ga1i Fyo, ap
ar, fne 8 behenika 0 pel 7ka (Yeroni-c
g, perqica) urine? The growth of Viola alpensis (Viola qrvensis) can be controlled by post-emergence application of υV on January germination plants.

5-amino-ni(3-chloro-5-trifluoromethylpyrid-2-yl)-4-cyanopyrazole with other compounds of general formula 1? I decided to use /I for convenience, and I decided to use the same hydrating property as the above one.

An aqueous suspension was prepared from the following ingredients: 5-amino-1-(3-chloro-5-trifluoromethylpyrid-2-yl)-4-cyanobinzole
50 w/W X Eteran B CP
1. Ow/v% Sobrobon 'I'
36 (sodium salt of polycarbonate)
0.2 w/v% Ethylene glycol 5 w/v% Logigle 23 (multi-branched xanthan gum powder fdJ) 0.15w/v% Distilled water Make it to 100%.

In preparing the above concentrate, the ingredients were mixed together and layered in a ball mill for 24 hours. The concentrate thus obtained was submerged in water and applied with shavings of 500 g of aqueous 7-shuiso thick material per hectare in spray solution 2001 to control the growth of Yaemugura, Veronica versica. The growth of Viola alpensis (Veronica arvensis) can be controlled by post-emergence application in germinated autumn crops of barley. Similar aqueous concentrates were prepared in the same manner as above, using other compounds of general formula I in place of -trifluoromethylpyrid-2-yl)-4-cyanopyrazole. Can be a friend.

In experiments on herbicidal activity conducted on representative compounds of general formula I, the following results were obtained: Test method Test procedure
This is also prepared by dissolving the test compound in acetone. The application was carried out using a standard laboratory insecticide sprayer, and its po 71.8 m, p, h, (2,9 Km/hr,
) using a flat fan exposure jet that delivers 540 tons of spray liquid per hectare;
11it fog pressure i2. sh/1 (a7 bond/1nc
h2).

The weight of the test compound is 0.0 in the test compound in 241 nt.
89 g [corresponding to an application rate of 2000 test compounds per hectare] and 500.1
Bath solutions corresponding to 25.31 and 8 g/h/h were prepared by successive 4-fold dilutions with acetone.

(b) Weed suppression type 1 potted compost in a 7 d plastic pot before light budding (
Weed seeds were sown on the surface of a bed consisting of 7 parts by volume of sterile loam soil, 3 parts by volume of beetroot and 2 g of sandstone imitation sand.

The amount of seeds per pot was as follows: Number of seeds of type D weeds/pot (1) Broad-leaved weed Chenopodium album
50 Brassica Cavell
kaber) 30-40 Ichibi (Abutilo)
n theophraati) 15 Malva Morning Glory (Rinfung Purpurea) 8
11) Ec
hinochloa crua-galli)
30 specimens were applied as described above and the seeds were loaded with 25-sharp sand for spraying. Taniza 4. One pot of apex was assigned to each treatment: no spray control and acetone only uXg control. After treatment, the mixture was kept at a temperature of 100 ml and poured 7 liters of water on top. Twenty days after spraying, two visual evaluations of 4% extinction were made compared to non-sprayed controls. The % weed eradication values were then plotted against the application rate, and the effective EDoo per hectare resulting in 901% eradication of weeds was then expressed as the q number. The results obtained are shown in Table 1.

(e) 4-suppressing 4 seeds after germination, growing 4 seeds, and growing 161 seeds in a plastic pot at the stage of oats, except for 1 year of oats. were sown directly into the test pots and no transplants were made beyond row I. These other substances were then allowed to grow within the reef, and then all test compounds were concentrated. The number of plants in one pot and the formation of the proboscis during spraying are as follows: (1) Broad-leaved weed Shiroza 4 4-leaved Brassica cabel 4 2-leaved Ichibi 3 Tech ~ 2-leaf Marupa morning glory 3 2-leaf (
11) Grass and sedge weeds Oat 10 1-2 leaf grass 4 1-2 leaf Cyperus eaeulent
us) 3 2-3 leaf trials were carried out in the same manner as above. One pot of each weed type was assigned to the unsprayed control and acetone only sprayed control trough treatments. Because of the spouting, keep these pots in the greenhouse, IIj
24 hours after the fog, I started using all of the water. Visual evaluation of % weed eradication compared to unsprayed controls was performed 020 days after spraying. Next, the value of ED, expressed as 7/ha, was determined as above. The results obtained are shown in Table 11 below.

Symbols for weed types (a) Broad-leaved weeds Ca = mini-chiroza = Brassica cabel At - Ichibi 1p = = Malpa morning glory (b) Grass weeds Af = Oat gc = Dogweed te) Carex weeds Ce - Cyperus vol. ■ Table 1 The symbols marked in the table above have the following meanings: ・r 1゛,
C,, -M J-Test compound, ・FA, R, So/
haJ=Application allocation used in the test (9/ha) “〈”=not @kai.

In view of the features of the present invention, compounds of general formula 1 in which R1 and R2 each represent an aqueous atom and RJI has the above meaning, i.e., R3 in Toyonaka herein has the above meaning. The compound of the formula IAO, in which BB has the above meaning, is the compound of 2 shown herein (i.e., 3-chloro-5-trifluoromethylpyridol-2-ylhydrazinomethylenemalononitrile). 9) A process consisting of caging the body. The cyclization is carried out in an inert organic solvent, such as an alkanol having 1 to 4 carbon atoms (e.g. ethanol), vinegar or ethoxyethanol, at room temperature to the reflux temperature of the reaction mixture. I can do it.

Is the compound of formula ■ the compound of formula V shown in Toyonaka in this specification? ! :V (3-chloro-2-hydrazino-5-trifluoromethylpyridine)
or its v1-dimensional salt, R' represents a straight-chain or branched alkyl group containing 1 to 41 carbon atoms, preferably ethyl, and the general formula (2) shown in the text of Example 2. It can also be produced by reacting with other compounds.

Reaction of compound of general formula V and compound of formula ■
In the presence of an inert chemical agent, such as Vi, an alkanol having 1 to 4 carbon atoms (e.g. ethanol, acetic acid or ethoxyethanol), optionally alkaline at room temperature or at the reflux temperature of the reaction mixture. It can be carried out in the presence of an acetate, carbonate or bicarbonate of the gold PA (e.g. sodium or potassium) or an alkoxide having 1 to 4 carbon atoms (e.g. ethoxide). When used, of course, the reaction with the compound of general formula (2) is carried out in the presence of an acetate, carbonate or anhydrous salt of an alkali metal (for example, sodium or potassium).

R1 or the above meaning **-r is a fragment of the formula IA, and in other embodiments of the present invention, f'L is a chemical compound of the formula V, a compound of the general formula (III), and a compound of the formula IA. The second intermediate compound can be produced without isolating it from the reaction mixture. Formula V
When the reaction of compound 8- with compound 8/IJ of general formula i is carried out in acetic acid in the absence [or presence] of an acetate of an alkali metal (e.g. sodium or potassium), a compound of formula IV Intermediateization 8 The intermediate compound of general formula IV in the reaction medium can be separated from the reaction mixture depending on the degree of bath temperature, and is preferably isolated according to necessity, so it is preferable to keep the temperature of the reaction mixture at a minimum. By heating in an inert organic bath agent (for example, ethoxyethanol), a compound of formula IA can be cyclized as shown above.

The compound of formula V exhibits similar herbicidal activity to the corresponding compound of formula IA which can cyclize this n, and the herbicidal activity of the compound of formula 1v is similar to that of the compound of formula IA. I think it will happen.

11 of this investigation! According to the characteristics of I, R1 is g'c (=
o) - group (here, R8 is a non-aqueous atom as described above for R4) (+-, t is a water-based atom or R''
C(=O)- group (where R8 has the meaning of above, R
A compound of general formula 1 in which the group R'' shown in 1 is the same as C(-〇)-), and R3 has the above meaning, that is, R' is the same as g'c(= o,)-group (where R8 is above d
Shoulder your own tentacles)? and R10 is an aqueous atom or an R'C(=O)- group (where R8 has the above meaning and is required within the definition of the symbol R9 and is the same as the group represented by the aqueous formula R8) ), and further R3 has the above-mentioned meaning, and from the compound I of the general formula IB mentioned herein, gJ has all the meanings of the above i. and R8 is a compound of the Issei formula (3) shown in the present specification which has the above seven flavors, or R8 is a compound of the above-mentioned W
A compound of general formula 1 having its own meaning and suitably an inert M
Sea bath additives, such as Kutono (Tomba Acetone), Yoshi 4j
The presence or absence of hydrocarbons (such as benzene or toluene), chloroform, dichloromethane, or dimethylformamide, and if necessary, a sweetfish drinker,
Even if V1 bilin, triethylamine/or ashes of alkali metals (such as sodium or potassium) v
= If bicarbonate is present, incubate at 0°C to the reflux temperature of the reaction medium to make a cultured reaction rice.
f:, or depending on the piercing use of the compound of the general formula IB (where R9 represents the above-mentioned Sato and BiO represents an aqueous atom or R8C (= O)-
In this example, R8 is prepared by adding a small number of compounds having the above-mentioned constituents. If desired, alkali metal complexes of compounds of the general formula I can also be used. According to other compounds of the present study, R1 is a"c(-ri1, where R is an aqueous R2 represents a hydrogen atom and R3 represents the above meaning. A compound of the general formula IC is preferably a compound of the formula IA having the above-mentioned flavor. It is prepared by reacting the reaction mixture with formic acid at the reflux temperature of the reaction mixture.

Other %clt of the present invention, 1rLvf, R1 or RC
(=O,)- group (where R represents all water atoms),
A compound of general formula I in which R2 is a hydrogen atom or a RC(=O)- group (in which R is a Mizuki atom with all 7F atoms, RJ has the above meaning J-, and R11 is a water-based atom) Or remove the HC(=0)- group and change the meaning of ftl to M
For the compound l of general formula 10 shown herein, R3
A chemical compound of formula IA having the above meaning Lj) in the absence of a suitable inert substance, such as acetone or an aromatic hydrocarbon system (such as benzene or toluene) or, if necessary, binder agents such as pyridine, triethylamine, or alkali metals (such as sodium or potassium dicarbonate or bicarbonate) may be present at 0°C or more. Selected anti-LC; Depending on the excess of anhydrous formyl surface, the general formula II) (wherein R3 has the abovementioned meaning and R11 is a hydrogen atom or n
It is produced by obtaining a compound of c(=o)- group).

Other than non-g+: Lnpo in rf character, R1 is kL'C(-〇)- group (here R' has the above meaning) all shown R
a compound of general formula I in which 2 represents a hydrogen atom and R3 has the above meaning, that is, B12 represents a R'C(=O)- group (
where R' has the above meaning and R3 has the above meaning.
The compound of formula IB (wherein R3 and R9 represent the above-mentioned M) is expressed by the symbol R1° and 7'LfCR. "C (also υ group or formula 11) (where R1 has the above meaning M) selectively removes the nHC(-〇)- group represented by the symbol R11, that is, the compound of the general formula I (Here, R1 and R2 are respectively n R'C(=o) -62, and R
1 by selectively hydrolyzing the compound (R4 has the above meaning M) under mild conditions to convert one of the groups g'c(-o)- to a hydrogen atom. Manufactured.

Hydrolysis can be carried out, for example, by treatment with an aqueous-ethanolic bath or suspension of an alkali gold pA (e.g. sodium or potassium) carbonate salt or with aqueous ammonia.

According to another feature of the invention, R1 or Rc(=o)-group (
Here, R is 7 as above for t (i ~ 41 carbon atoms + 1 degree or minute + f
7. All the alkoxy groups in the chain are shown), and R2 is water: N
,, represents an atom, and R3 is a compound of general formula 1 in which the meaning of Compounds of the drug formula IF shown in the above specification and in which B3 has an upper ml concentration and total M have the R15 force and group.
"c (-o) (B16 represents a group forming a circle defined by R14 above or a phenoxy group), and R3 has the above meaning /'1", the general formula IG shown in this document
B15 is converted into a water-based atom by reacting the adduct with the compound of the general formula (3) shown in the present specification, in which R1' has the above meaning, and one of the groups represented by the symbol R15 is converted into an aqueous atom. group R1
6C(=O) −': When R1111 is phenoxy &'fr, the other group represented by the symbol R1 is B
Indicates a group that is necessarily in the fixed position of IJ, and if necessary, ru ill represents a group g”c (=o), and R11l is R1
The symbol R1' is shown on the platform that indicates & within the fixed time of 4.
If other groups are represented by n groups represented by the symbol R13! I'll leave it to you to manufacture it. As one skilled in the art will appreciate, the general formula IF
The desired compound can be obtained by selecting the appropriate compound of the general formula IG and IX. The reaction may be carried out in water or in the presence of a suitable inert aqueous or organic bath agent, e.g.
Refluxing of the reaction mixture at room temperature in an alkanol containing ~4 carbon atoms (e.g. ethanol, a small or aromatic hydrocarbon (e.g. benzene or toluene) or preferably in a soup of the general formula (2)) At the same time, it can be treated with a knife pressure FK if necessary and a base if necessary, such as an alkali Kanabashi alkoxide, such as a compound of the general formula (2).

Another feature of the present invention is that xn is such that R1 represents an R'C(=O)- group (herein has the above meaning) and H-2
'c(==o)-group (where R' has the radical r) and denoted by R1 'f? :, R'C(=O)-
R6 is the same as the group, but it does not matter whether it is 6 or different.
Compounds of general formula 1 having the meaning of d, ie R"J?
Does HJZ have the above meaning and Bl? is rc
(=o) - group (herein has the above meaning)
It'c (-=
The compounds of the general formula IH mentioned in this specification, which may be the same or different from the LJ )- group, are represented by the general formula IB (where R3 has the above meaning and RlG represents an aqueous atom) or a compound of formula IC (where R3-.1
A compound with the general formula In() that reflects the above meaning;
Here, R1 stands and R12 stands for the upper shrub.)
Compounds of alkali metals (e.g. sodium or
The anhydrous formyl derivative is prepared by reacting it with the general formula l/M (where R82l and X have the above meaning, of course. This may be carried out in a suitable afrotic solvent, such as dimethylformamide, at laboratory temperatures or at temperatures remote from the reactant.

In another case of non-invention, R12 and R2 together become -co-(cRalb)m-co-*= and R
4゜■? ab The compound of formula 1 has the above meaning tM - The compound of formula 1 is )<3 has the meaning above - The compound of formula IA is x, a', Rb A compound of the general formula
A compound of the general formula shown in Toyonaka herein, which has the benefit of upper ne+, and a suitable inert organic bath agent, such as a chthone (e.g. acetone), an aromatic hydrocarbon (e.g. benzene or in the absence or presence of chloroform, dichloromethane or dimethylformamide (toluene), chloroform, dichloromethane or dimethylformamide and, if necessary, purifying agents such as virididine, triethylamine, carbonates or bicarbonates of alkali metals (e.g. sodium or potassium). It is produced by reacting in the presence of a salt at 0° C. to the reflux temperature of the reaction medium. If desired, alkali metal derivatives of the general formula IA can also be used.

The alkali metal scrap compound of the compound of general formula IA or IE can be prepared by general formula 1 or Ig (here, R3 and R12).
has the above meaning) in an inert, aprotic bath, such as dimethylformamide, at room temperature or the reflux temperature of the reaction mixture. ) can be produced in situ by reacting with hydrides of I/um or potassium).

Another feature of the invention is that R1 is a group R5 (wherein R5
has the above meaning), R2 represents a hydrogen atom or the above-mentioned R6, and R3 has the above meaning. R1?
represents a hydrogen atom or a group within the meaning of R6 above, and R3 and R6 have the above meanings. The adducts of the general formula IJ shown in Toyonaka herein are: A compound of the general formula (2) shown in Honmei Masaoka, which has the same meaning and R18 is a straight or branched alkyl group having 1 to 41 carbon atoms, preferably l is ethyl.
It is produced by reacting with a compound of the formula V shown in Toyonaka herein, in which R3 has the above meaning, or a Shichino Jaku addition salt, such as Iki salt.

The reaction of the adduct of general formula (I) with the adduct of formula V can be carried out using a suitable inert organic bath, such as an alkanol having 4 carbon atoms (e.g. ethanol, O1' or ethoxyethanol). At room temperature, at the reflux temperature of the mixture, and if necessary in the presence of vinegar salt, charcoal salt, or charcoal salt, with an alkali-based base (e.g., sodium or potassium). General formula V
The compound of the chemical compound cough salt τ is used in one pot, and the compound of the general formula ■ is anti-L6t with alkali metal (e.g. sodium or potassium salt, carbonate or carbonate). Attached to the existence of

In another embodiment of the present invention, vJ, gl represents the group R6 (where l (6 means /), R3ρ, the above; omitted atom or iself number R
A compound of the general formula I that is the same as the group R5, which is the same as the group R5, which is the same as the group R5, that is, R6 has the 1st taste of Kaminichi and R5B is a water-based base. Is the adjunct of the general formula IK in which the same expression as the group R'' is shown in the main text of the main text? In the present invention, R5 has the above-mentioned meaning M and Xl represents an atom, bromine or iodine atom r. General formula
1 mole or 2 moles of the IO adduct and a suitable inert organic bath agent, such as aromatic hydrocarbons (such as benzene or toluene), chloroform, dichloromethane, tetofhydrofuran or dimethylformamide, or In the presence of η, optionally a tackifying agent such as pyridine, triethylamine, an alkali metal (e.g. sodium or potassium) carbonate salt;
The analogy is 15-Kurakun-5 (1, 4, 7, 10°13
-pentaoxacyclopentadiene) %L<18-crown-6 (1,4,7,10,13,16-hexaoxacyclopentadecane)] at 0°C to a distance from the reaction mixture. It took nine hours to create a core at temperature T. The preparation of compounds of the general formula IK in which R is the same as the group R6 is convenient if an excess of the compound of the general formula XI is used. What is required is 1. A mixture of compounds in which R in the general formula IK represents a frozen confection atom and compounds in which R represents the same group as R6 is separated by known methods such as crystallization or chromatography on silica gel. be able to.

In still another embodiment of the present invention, R' is a group R1aR"
C1(-(CCTER18oj hiR"" is -f:n6v
) M pieces of carbon atoms together with 1 to 8 carbon atoms and unplaced 77) or Xian Hong, Hydroxy 4 丞, 1 to 6 ivA carbon atoms in page order or branched alkoxy group, carboxy group, 2-9
Straight chain or branched chain alkyl having M carbon atoms/
carbonyl group, and also a group consisting of 7 or 11 or more halogen atoms (even if the halogen atom is a straight or branched chain alkyl group). , 1 indicates all the Mizuki atoms, R3B's the incarnation of the general formula 1 with the above Emikai, and the incarnation of the general formula 1 with the above Emikai, R3 gas Jaku Kohi BI Q has the above Emikai in the present Meigetsu 4II Kutsu A compound of the general formula IL shown below, R''.

g 1 B and gl'' are produced by reducing the imine residue of the compound of the general formula X shown in the unknown details. Reduction of imine groups 1. Water-resistant alkali compounds (for example, sodium) can be made water-resistant by cyano-water-based compounds. The presence of an alkanol (such as methanol or ethanol) or tetrahydrofuran with -S,
It is possible to do this by sucking the Kansei fan of the reaction mixture in the room.

Other features of the invention! t means that R1 is a group R5 (where R
A compound of general formula 1 in which R2 represents a frozen candy atom and RJ has the above meaning, that is, R'J-R6 or The monsters of the general formula IM shown in the present specification, which are used for one's own laziness, are R20 or 1~
Straight-chain or branched noalkyl or alkoxy group with / of 4 carbon atoms and g! 2, chiR6ρ
・General formula
The group R"CO- of the compound of v is produced by removing it. When R20 represents an alkyl group, the removal of the group R"Co- is carried out by optional hydrolysis with a mild alkaline condition F. Or, if R20 represents an alkoxy group (e.g. L-butoxy group), it is a mildly alkaline or dazzling agent, such as an alkaline fluorophore (such as sodium or Hydrogenated product of potassium chloride, dissolved in water or in a suitable inert organic or aqueous solution.
l = 1 bath A'l, for example lower alkanol (fC and methanol) or water and 1 lower alkanol (
For example, water and lower alkanols (methanol) may be treated in a mixture with an inorganic substance, e.g. ) and 06♂' in the laboratory at the temperature of the reaction mixture. As is clear to those skilled in the art, R5 in the general formula Xv is Alco 1
When replacing an alkyl, alkenyl or alkynyl group with a xycarbonyl group, the group it"co-
The removal of is accompanied by hydrolysis, or when a lower alkanol is present in the reaction medium, the reaction is carried out with the general formula In (where R6 is an akekyl, alknyl or alkynyl group substituted with a carboxy group, or R6 produces a compound in which the alkoxy moiety is the same as that of the lower alkanol present in the reaction medium, and the alkyl, alknyl, or terkynyl group is directly lower than the alkoxycarbonyl group. What is done with the alkoxycarbonyl ester parent ρ) depends on the reaction conditions used.

The term "lower alkanol" that is used in the unknown is mostly ash-based atoms of 91 to 41 solids, which are not used in general. M
means an alkanol. .

In the waiting row of the uninvented song, R1 is used and R2 is used.
′扛Menaraki? Compounds of the general formula 1, where Ra has the meaning above, and Ha has the meaning above, are produced by reacting with formic acid with any amount of IJτ acetic acid. This reaction can be carried out from 0°C to reflux of the reaction mixture (R( m required V trowel, force 11 depending on the required wheat
It can be done by pressing.

According to another characteristic of non-invention, the Rlh) group cH2it''(
Here, all is 1 to 7 ash: i7-, atom tML, and cyano, hydroxy group, 1
A straight or branched alkoxy group having ~6 carbon atoms or one or more than 7n atoms, such as a straight or branched chain alkoxy group having 7 or more carbon atoms, e.g. The general formula (■) in which the alkyl fundamental sound ``bo'' (3-) is removed, R'' is an elementary atom at 7, and R3 is the same meaning as above is the general formula The compound of the general formula IN shown in Part A of this specification, which has the meaning of hiR71 or upper order, is
R3 and R21 are added by reducing the carbonyl group of the compound of general formula X shown in the unclear details above. The reduction of the carbonyl group at the chemical base of the general formula ethanol) or tetracyhydrofuran at room temperature, and the main reaction mixture is heated at a distant current.
I can do 1.

If R''+R18 and R19 have the above meanings, the compound of the general formula
6 Unknown The compound of the general formula xvn shown above can be produced by reacting with a substance. This formation occurs in the presence of lower alkanols, such as methanol or ethanol.
If necessary, the LCJ reaction may be modified, for example, in the presence of hydrochloric acid or hydrochloric acid, at the experimental temperature or the reflux temperature of the reaction mixture.

R', lzeokobi R'' means the above meaning of M-J-Ruzu Thumb Xv. The compound of the general formula This reaction can be prepared by reacting with a compound of the general formula Room temperature 1 to 6 farts is υft (
The reaction can be carried out with a base, for example, triton B.

The alkali gold W4 compound of general formula XVM is BA
General formula Xv with 7 leech beds for construction R20ρ and above
can be cleaved in situ by reacting the compound with a hydride of an alkali metal (such as sodium or potassium) at laboratory temperature to the reflux temperature of the reaction mixture.

R3's construction Boo is the best'' General formula Xv with its own 7-value taste
The compound of (2) is a compound of the formula IA in which R8 has the above meaning, R20xr): a compound of the general formula XX shown in Honmei Jokuso, where x has the above meaning, or R2G has the above meaning. A compound of the general formula
In the absence or presence of chloroform, dichloromethane or dimethylformamide, and necessarily in the presence of sterilizing agents, such as pyridine, triethylamine, 1fC is a carbonate of an alkali metal (such as sodium or potassium) or a salt of icy carbon. It can be produced by reacting in the presence of F at 0°C to the reflux temperature of the reaction product.

The compound of the general formula General formula XXI shown in this specification has its own meaning
It can be produced by reacting with a compound of This reaction 7 can be carried out in the same manner as described above for the reaction of the compound of the general formula IA with the compound of the general formula XX and the compound of the formula IA.

R2 (compounds of the general formula
f and R■ is 1 to 4 (1i1 carbon source gold/stagnation +
[d or represents a branched alkoxy group, RJ retains the above meaning, and 8 units represent a phenoxy group, and mM represents the above, Compounds of the formula XXv as shown herein which have a taste of M can be prepared by reacting with compounds of the general formula XXvI in which R22 has the above meaning M. The reaction can be carried out in water or in a suitable inert aqueous or aqueous solvent.
For example alkanols with 1 to 4 carbon atoms (for example ethanol) or aromatic hydrocarbons (such as benzene or toluene) or preferably of the general formula XX
VI.

In excess of the compound, at room temperature to the reflux temperature of the reaction mixture and if necessary under pressure, a base, such as an alkali metal alkoxide, for example of general formula XX
This can be done in the presence of a compound of VT.

The soup of formula XXV has the formula (where RJ is the above,
The adduct of A can be prepared by reacting it with a compound of the general formula XXvfi shown herein in which R23 and X have the meaning of dd above. This reaction can be carried out in the same manner as described above for the reaction between the compound of 2IA and the compound of general formula XxO.

According to another feature of the invention, R1 is an alkoxycarbonyl group R6 which can have 2 to 9 carbon atoms.
and t is a water-based atom or alkoxycarbonyl having 2 to 9 carbon atoms, and also represents a radical 6, and R3 has the above-mentioned meaning. is an alkoxycarbonyl substituent group e%R1 with an alkoxy moiety different from the alkoxy moiety of the group R6 shown in R2 within the above definition.
Alkanols having 1 to 8 carbon atoms (e.g. methanol) can be prepared by transesterification using an excess of alkanols having 1 to 8 carbon atoms (e.g. hydrochloric acid) existence of F
Experiments can be carried out at room temperature or at the reflux temperature of the reaction mixture with K and optionally with the intervention of water.

4i: Another feature of the invention is that Ln is an alkoxycarbonyl substituent having 2 to 9 carbon atoms, and t is an aqueous atom or 2 to 91 carbon atoms. Compounds of general formula 1 in which the alkoxycarbonyl substituted group 1 is represented by R1, and B and a have the above-mentioned meanings include the group R6 represented by R1.
is a carboxy substituent fL, and R2 is an aqueous atom or carboxy+ is a group R+l. The esterification agent can be prepared with an alkanol having 11 carbon atoms. This esterification can be carried out using an alkanol containing 1 to 8 carbon atoms in the presence of an esterifying agent, such as a mineral acid, at a temperature varying from 2 to 2 mL of the reaction mixture. , according to another feature of the invention, W is a group RE (where R6
has 1 to 8 carbon atoms. f chain or branched alkyl group, or straight or branched alkoxy group with 2 to 8 carbon atoms and cyano group, hydroxy group, 4-f' with 1 to 6 carbon atoms. , a carboxy group, or 11 or more halogen atoms
(represents an alknyl or alkynyl group derived from Naohonggi, which is expressed in the present specification), where R2 is a frozen confection atom and R1 has the above meaning. In the compound of general formula 1, R3 has the above meaning, and R1 is a straight or branched alkylene group having 1 to 8 carbon atoms or a group having 2 to 8 carbon atoms. a straight-chain or branched alkoxy group in which R24 has 1 to 8 carbon atoms, is unsubstituted or has 1 to 8 carbon atoms; One or two straight-chain or branched alkyl or alkynyl groups having 2 to 8 carbon atoms; (Here, the amino group is substituted with an alkynyl or alkynyl group of 21vA, and the fC field is the same, but they can be used even if they are rarely different.)
, an alkoxyamino group in which the alkoxy moiety has 1 to 8 carbon atoms and may be straight chain or branched; an alkoxyamino group in which the alkane moiety has 1 to 5 carbon atoms and may be straight chain; An alkanesulfonamide group that can be branched or branched.
or a Hat group (where Hat has the above meaning tl'e).
Prepared by reacting the adduct of the general formula xxxiO shown in the present specification in which R''b-L and R3 have the above meanings with the adduct of the general formula XXXIV having the above meaning. or when R14 represents an alkanesulfonamide group, the alkali metal (fc and il) of the alkanesulfonamide shown by the general formula
-['Can be produced by reacting with sodium chloride salt. When R2' represents an alkoxy group, this reaction may be carried out with an excess of intervening alkanol represented by the general formula When substituted with an alkynyl group, an amine group, an alkoxyamino group, an alkanesulfonamide group or an f(et group), the presence of a suitable inert organic solvent, such as a ketone (for example methyl ethyl lactone), dimethylformamide or toluene. F
In addition, if R24 is an alkoxy group or a plucansulfonamide group, a base such as an alkali metal (
For example, the presence of carbonaceous salts of potassium) F-[, or B1
carbonate of an alkali metal, such as potassium, or an excess of ammonia, heptano or di-alkyl-, alknyl- or alkynyl-amine, if 1 represents an unsubstituted or substituted amino group or Hat group or alkoxyamino group; Due to the presence of an alkoxyamine or a compound of the Enoki Iso formula represented by the general formula is a straight-chain or branched alkyl group having 1 to 8 carbon atoms (il''M) and substituted with a carboxy group,
or a chlorinated compound of the general formula 1 having 2 to 8 carbon atoms and having a straight chain or (branched alkenyl or alkynyl group) τ which is directly substituted with a carboxy group. Thionyl again. It can be produced by reacting so-called oxidized melon in the presence of an inert organic solvent, such as toluene, if necessary, at laboratory temperature or at a remote current temperature of the reaction mixture. With FJT violet, the compound of the general formula mI can be prepared in situ and reacted with the compound of the general formula ■■ without isolation. R1 is the group R11 (where R
6 is a 11- or 21-carbon alkyl group having 1 to 81 carbon atoms, respectively, and an aminocarbonyl group substituted with C, and 1) having 1 to 8 substituted carbon atoms. carbon atomic sound M
or a straight-chain or branched alkyl group having 2 to 8 carbon atoms or an alkynyl or alkynyl group having 2 to 8 carbon atoms, R1 represents a water atom, and R1 represents a
Convenient method for preparing compounds of general formula I in which the meaning of P is M
R1 is a group R6 (where R6 is a straight or branched alkyl group having 1 to 8 carbon atoms which is directly substituted with a carboxy group or a carboxy group).
A compound of general formula 1 representing a straight-chain or branched alk, nyl or alkynylene having ~8 carbon atoms (7barf) is combined with an oxy salt (1) of a suitable heptano- or di-alkylamine. The reaction is carried out in the presence of potassium charcoal at laboratory temperature or at the far υfL temperature of the reaction medium.

Compounds of the general formula XxXI include R' and R
′ is combined with the yatom which is itself ftj to form the general formula +1 (in the formula, Ro, Rd, Re, Rf, R”, R”
Ohjhin has the above meaning)
A compound of general formula 1, in which a has the above meaning, is treated with anhydrous ice cream in the presence of an inert organic solvent, such as chloroform, at laboratory temperature or the temperature of the reflux of the reaction mixture. It can be manufactured using

Other features of the present invention may be incorporated herein by reference: R1 is a group R5 [wherein R5 is an alkanesulfonamidocarbonyl group (wherein the alkyl moiety has 1 to 8 carbon atoms and may be a straight chain). [Indicates a straight-chain or branched alkyl group having 1 to 8 carbon atoms, which may be branched]
, R2 represents a hydrogen atom, and 1 and 3 have the above meanings, ie, ar and R
A book in which 3 has the above meaning and To represents an alkanesulfonamide group (wherein the alkane moiety has 1 to 8 carbon atoms and may be linear or branched) In the specification, the formula IQ is a compound in which R1 is a group R6 (where R5 is 1 directly substituted with an unsubstituted aminocarbonyl group).
Straight-chain or branched alkyl having ~8 carbon atoms, S or straight-chain aminocarbonyl group substituted with C and straight-chain or branched chain having from 2 to 8 carbon atoms Compounds of formula I in which 3 represents the above-mentioned meaning and R2' represents an unsubstituted amine group;
Preparation by reacting a compound of P with an acicanesulfonyl chloride in which the aryl moiety has 1 to 8 carbon atoms and which may be linear or rarely branched. I can do it. This reaction takes place at laboratory temperature or the reduction of the reaction mixture υ+c
If necessary, add a suitable inert organic solvent such as a ketone (e.g. methyl ethyl ketone) or toluene and, if necessary, a base such as an alkali metal (e.g. potassium). It is possible to have trouble with the existence of

In addition to the present invention, if there is a modification to the violet, gl is base 6 (here R5
has 2 to 8 carbon atoms separated by a hydroxy group
1 m-chain or branched alknyl or 9 alkynyl group bearing 3 to 81 carbon atoms attached to a straight-chain or branched alkyl group or hydroxy group , R2 is hydrogen atom 7J\ and k
Compounds of the general formula (3) in which La has the above meaning M'', that is, R3 is the above-mentioned compound, and R8 has 2 to 8 carbon atoms, and is a head or branched chain. Compounds of the general t + formula IR shown herein which represent an alkylene group or a straight-chain or branched alkenylene or alkynylene group having 3 to 8 carbon atoms, R3 has the meaning given above, and R or1~
straight-chain or branched alkylene radicals with 7 carbons g) jA-f- or with 2 to 7 carbon atoms ++!
Indicates a chain or branched alkenylene or alkynylene group, where ♂ is a hydrogen atom or a straight or branched alkyl group having 1 to 8 carbon atoms.
Carboxylic acid or ester group of the compound of the general formula ■W in which l represents a hydrogen atom (i-reduced, that is, RU represents an alkyl group and T1 represents a group EL25 (C=1)) - (where 81 is (representing a linear or branched alkyl or alkoxy group containing 1 to 4 carbon atoms), it can be produced by such reduction. If aU represents a hydrogen atom, this reduction is dihydrobis-(2-
Me)xy-ethoxy)aluminated sodium trisomate is used in the presence of a suitable inert organic bath, such as toluene, at laboratory temperature or by refluxing the reaction mixture. If Ru is an alkyl group, this reduction can be carried out using sodium borohydride in the presence of methanol and L-butanol as bath agents at the reflux temperature of the reaction mixture.

If there is another waiting time for non-invention, gl is the law R5 (here R6
is a straight-chain or branched alkyl group having 1 to 8 carbon atoms substituted by a chlorine atom or a straight-chain or branched alkyl group having 2 to 8 carbon atoms substituted by a chlorine atom. branched chain alknyl or alkynyl group)
In the compound of the general formula 1 in which B2 represents an aqueous atom and R1 has all the above-mentioned meanings, that is, the compound of the general formula Is shown in the present specification in which B3 and ar have the above-mentioned meanings, R'' is Group R5 (where R6 is a straight or branched alkyl group or a hydroxy group consisting of 1 to 8 R atoms attached to a hydroxy group)
-3 represents a 1M chain or 7-branched alknyl or alkynyl group having 2 to 8 carbon atoms,
If R2 represents a hydrogen atom, a compound of general formula 1 having the above-mentioned taste is mixed with thionyl chloride and, if necessary, in the presence of a suitable inert solvent such as dichloromethane or trichloromethane. It can be produced by reacting at a temperature of 1 degree or reflux of the reaction mixture.

Others of this invention! # If t″L, R1 represents a group R8w, and R5 represents an alkylthio group (here, the alkyl portion is 1 to 4
of general formula 1, in which R'' represents a hydrogen atom, and R1 has the above meaning τ41r. Compound, Dinawara R
The compound of the general formula IT shown in Example #I, in which R7 represents an if-chain or branched alkyl group having 1 to 41 carbon atoms, is kLJ. is the alkali metal (e.g. sodium or potassium) of the compound of general formula IA in which tH2 has the above meaning. Even if the branched chain is not present, the process may be carried out in the presence of a suitable inert organic bath agent, such as toluene, and optionally a crown ether, such as 15-crown-5 or 18-crown-5, while cooling to 0°C. - It can be produced by reacting in the presence of Crown-6.

According to another feature of the invention, the W-type R2 together with their attached family atoms form a group of the general formula XXX11 (
where R9 represents a linear or branched alkoxy group of 1 to 4 carbon atoms (RQ is the above, south of the base body), and R1 is the above, broad 3- Compounds of formula 1, i.e. R', f and q ・R or upper i's meaning #: Compounds of general formula IU which are mixed in Honmei Yasei in which Ba is upper d's g taste k ! -f expression 1
A human compound is represented by the general formula XX shown in the present specification, where l is the above-mentioned, M is the taste, and Rw is a water-based atom or a straight or branched alkyl group having 2M of 1 to 4 carbon atoms.
Compound B of X11, for example in the presence of an acid catalyst (for example p-)luenesulfone, [and optionally in the presence of a suitable inert organic solvent such as tetrahydrofuran or dioxane, at a temperature of 21°C of the reaction mixture. It can be produced by reaction. This reaction can be carried out at laboratory temperature or at the reflux temperature of the reaction mixture in the presence of a lower alkanol (e.g. methanol or ethanol) and optionally in the presence of a lower alkanol (e.g., warmer or less acid). can.

According to the song standby of the present invention, Le 1 J = - and Le 2 are combined with seven sweaty protein atoms, and the general formula A straight chain with 1 or 21 carbon atoms and which may be the same or different.
Of course, a branched alkyl group and a straight amine group,
The compound of general formula 1 in which Rq stands for the above-mentioned abyss) and 81 has the above meaning is a compound, that is, Rx carries 1 to 4 carbon atoms. The compound of the general formula IW shown in this book, which represents a straight-chain or branched alkyl group and where g(l and UU have the same meanings as above, is R1
and R1 together with their bonded nitrogen atoms represent a group of the general formula ) Compounds of the general formula l having the abovementioned meaning and further in which R3 has the abovementioned meaning (i.e. yr<I, in the present specification where R'', R' and R have the abovementioned meaning).

A compound of the general formula IU can be a seven- or di-alkylamine (where the alkyl fraction -f:n each has from 1 to 4 carbon atoms and is rarely a branched group). and the reaction is carried out with the di-alkylamine.
It is also possible to react and charge the same or different substances. This reaction is carried out using a suitable non-depleting agent, for example, in tetrahydrofuran, at room temperature or in the reflux region of the reaction surface, preferably in excess of a monoalkylamine or a di-alkylamine. This can be done for the existence F.

According to another feature of the invention, n is R1 is a group g6 (where R
11 is a carbon atom in the 1 to 61 direction, or the carbon atom in the α position is directly substituted with a straight or branched chain alkoxy group.
τ indicates a frequent or branched alkyl group having 1 to 8 carbon atoms, R2 indicates an aqueous atom, and ＜8 indicates the above meaning. , that is, gJ is the above: M is a soft body, R' is an aqueous atom or a straight chain or branched alkyl group having 1 to 7 carbon atoms, and r2 is an aqueous atom or The adducts of the general formula IY shown in this KJAs, which represent a straight or branched chain alkoxy group containing 6 carbon atoms, are R3,
i? It can be produced according to the compound of the general formula XXXVI shown in the main part of this specification, where 1 and 2 have the same meaning as M. , this reduction is carried out using a suitable inert M sequestering agent, such as 1
It can be carried out in the presence of an alkanol containing ~4 carbon atoms (e.g. methanol or ethanol) or tetrahydrofuran at a temperature of ~60'C. When T2 carries out the reduction of an alkoxy group under mild conditions, R1 is a group R11 (where R6 spans 1 to 8 carbon atoms and the α position is 1 to 1). A linear or branched alkyl chain containing all 6 carbon atoms or a straight or branched alkyl group substituted with a branched alkoxy group
), R2 represents a water atom, and R3 has the above meaning 'M'!'.
A compound in which 2 represents an alkoxy group -) IY) is a strong, intense reduction 01 history, where R1 is a group R11 (where R6 is an undirected straight chain with 1 to 81 carbon atoms tM) or a compound of the general formula 1 in which R2 represents a hydrogen atom and R4 has the above meaning (i.e., a compound of the general formula IY in which T2 represents all hydrogen atoms); Give the compound ′@). If the reduction is carried out in the presence of alkanol F, this reduction is accompanied by alcohol decomposition of the alkoxy group represented by T2 in the general formula
At the position, the alkoxy group corresponding to the alcohol used is given an esterified raw material.

Another feature of the present invention is that R1 is a group R11 CR5 is a carboxyl group, P1 is a straight or branched alkyl group having 2 to 8 carbon atoms, 2 to A straight-chain or branched alkoxycarbonyl group lfc having 9 carbon atoms can be represented by a direct substitution or one or two straight-chain or branched alkoxycarbonyl groups having n1 to 8 carbon atoms, respectively. An aminocarbonyl group substituted by a branched alkyl group (where the aminocarbonyl group is substituted with two alkyl groups) is rarely the same. 1), or an aminocarbonyl group (where the aminocarbonyl group is a straight chain or branched alknyl or alkynyl group bearing 2 to 8 carbon atoms), or an aminocarbonyl group (where the aminocarbonyl group is '1 is a solid ralknyl or alkynyl group and 1 is represented by 1 (L and the like may be the same and β or different)], 2 is a water atom, and R3 is the above-mentioned atom. Compounds of the formula I, i.e., where gj has the above meaning and RZ is 2 to 8
represents a straight or branched alkylene group extending from 1 to 8 carbon atoms, and T2 is a hydrothousand group, a straight or branched alkoxy group extending from 1 to 8 carbon atoms, or 1 or 21 chained or branched alkyl groups having 1 to 81 carbon atoms;
/ζ amino group (wherein the amine group is a direct substitute for two alkyl groups, these groups may be the same or different) or 11vA or An amino group substituted with two straight or branched alkenyl or alkynyl groups and where
When two alknyl or aquinyl groups are substituted, the levels may be the same or different.・
The process R2 becomes one with the bonded nitrogen atoms of -f:n, resulting in Ro, Rd, R" + R' *f, process t"
The term "n" indicates a group of the general formula n having the above meaning, provided that the group of the general formula 9 excludes the carbon atom of the carbonyl group.
Compounds of the general formula I having 2 to 8 carbon atoms and in which R3 has the abovementioned meaning are each treated with an alkali metal (e.g. sodium If the aqueous solution of water (from l) is added to the aqueous solution, lower alcohol (l may be methanol)
Due to the presence of
Alternatively, a straight-chain or branched-chain alkanol having 1 to 8 carbon atoms is added with an ef-alkali completely annihilated lower alkoxide (
(e.g. sodium methoxide) or in the presence of water if necessary in an ethanolic aqueous chloride system? 11 degrees to the reflux temperature of the reaction mixture, or ammonia or a mono- or dialkylamine (where the alkyl moiety is a uf chain or branched group having 1 to 8 carbon atoms and the dialkylamine is fried in pieces). may be the same or different) or mono- or di-alknyl- or alkynylamines (wherein the alknyl or alkynyl moieties may be monolinear or branched, each containing 2 to 8 di-alknyl- or alkynylamines containing carbon atoms, which may be the same or different, in the laboratory, if necessary in the presence of an inert organic solvent, such as toluene, tetrahydrofuran or dioxane. It can be produced by processing the reaction mixture at a temperature that is lower than or equal to the reflux temperature of the reaction mixture.

General formula XX in which g”, Ry Okoji T8 has the above meaning
The compound of xv11 has the formula IA in which Bm has the meaning above.
The compound of the general formula XXXVI shown in the unknown plaster, in which the O compound t11 has the meaning of upper eye self, can be reacted with a substance to form T! is a water-based atom, or reacts with a compound of general formula XXXVI in which I has the above meaning to form a compound of general formula XXXVB in which T2 is an alkoxy group. It can be manufactured by generating. This reaction can be carried out under the conditions described above for the reaction of the compound of general formula X and the compound of formula IA.

The compounds of the general formula xxxv in which T1 represents a water atom are:
R' represents a group R5 (wherein R' represents an alkyl, alknyl, or alkynyl group substituted with a carboxy or alkoxycarbonyl group), <1 represents an aqueous atom, and R'' has the above meaning t4f; It can be prepared by the method described for the preparation of compounds of formula I. General formula xx in which T1 represents the group R15 (C=0) f
The compound of xv can be prepared according to the method described for the preparation of compounds of general formula XvO.

According to another feature of the invention, R1 and R1 together with their attached nitrogen atoms have the general formula R (where Rc
+ Rd, Re+ Rf+ Rg+ R'>, 1:
and n have the above meanings), and Ra has the above meaning.
r.

The manufacturing formula is prepared by a method consisting of treating the compound of general 2) shown in the present specification i[F1000] with a base, where Rf, Rg, Rh, R", X and n have the above meanings.The treatment with a base is , sodium hydride in dichloromethane or dimethyl sulfoxide, ethanol, potassium bicarbonate in acetone and optionally water, potassium carbonate in acetone and optionally water, triethylamine in water, or ethanol. If necessary, work in water in Triton B in the laboratory!
It is suitable to carry out the reaction at a certain degree.

In the compound of general formula XXVM, R' has the above-mentioned taste H-r
The formula IA is a monster, but the chlorine is also a monster! Indicates a bromine atom and FLc, Rd, R'', R', mg
, Rh'X $-Yohin is superior n's,! has a taste,
And Also, L< is the absence or presence of toluene, chloroform, dichloromethane or dimethylformamide, and optionally r+'' = a reaction mixture, such as pyridine, triethylamine or an alkali metal (such as sodium or dimethylformamide). 1) Noumuno's charcoal salt or heavy charcoal is a mixture of salt and salt (F)
T! #, cracked by reacting at temperature.

If necessary, the compound of general formula XXVI can be prepared in situ during the reaction of the adduct of formula IA with the compound of general formula XX and relaxed without isolating the compound of general formula xx1. After treatment with a base, R1 is combined with the nitrogen atoms to which it is bonded, forming the general formula B (where Ro, R
'l? , R' l R' l R”
has the meaning given above) and R3 has the meaning given above. Compounds of the general formula I can be produced.

In the general formula XXVIO, fh- and i-iriki-
or both represent hydrogen atoms and/or R
When the h0-force or both forces represent an alkyl group having an α-hydrogen atom, treatment of the compound of the general formula xxvi with a base results in, in addition to the compound of the general formula l, depending on the reaction conditions used. A compound having an open-chain alknylcarbonylamide group at the 5-position of the pyrazole ring (i.e., R"R"N-
represents an open-chain alknylcarbonylamino group, and RJ
A compound of the general formula 1 with the abovementioned meaning is formed, with hydrogen chloride or hydrogen bromide being removed and an ethylenic double bond being formed. For example, in the compound of general formula XXvl, when t has the above meaning and Rf is hydrogen, R"l Rd, R"l Rg, Rhl
The general compound shown in this specification which has the above-mentioned taste, R'' is the compound of the general formula In the compound of the general formula XXl'l, l represents an alkyl group having an α-hydrogen atom, and
When represents a hydrogen atom or an alkyl group having no α-hydrogen atom, in addition to the compound of general formula (■), R' + Rd+
Re+ Rf+ Rhl R3 has the above meaning, and Rj and Rk each have a hydrogen atom or a straight or branched chain having 1 to 3 carbon atoms, which may be the same or different; represents an alkyl group, Rj and g
There are two general compounds in which the total number of carbon atoms in k is 3 or less.

It will be apparent to those skilled in the art that other compounds of similar structure can be produced by the removal of hydrogen chloride or hydrogen bromide while forming an ethylenic double M, for example. In the general formula XX1l, 2 is an alkyl group having an α-hydrogen atom, and gh is an alkyl group having no water atom or an α-hydrogen atom. be able to.

Compounds of general formula I and pyrazole are directly related to Ef
A mixture with a chemical adduct containing all the alknylcarbonylamino groups of A, for example, a mixture of the compounds of the general formulas m and XXXI thus obtained, can be prepared by a known method. Components of the general formula I, such as those of the formula

(The term ``known per se'' used in this Example #I Toyonaka means a method that is conventionally used or a method that is described in the chemical literature.
From a compound of the general formula , for example R' + R' + R'' + Rfr
The compounds of the general formulas XXx and XXX[, in which Rg 口♂ + Rj + R' + K' and n have the abovementioned meanings, have the same 72 herbicidal properties as the compounds of the general formula 1.

A salt of a compound of general formula 1 in which R1 represents a group g5 (wherein R6 represents alkyl, alknyl or alkynyl converted to a carboxy group) with a base that can be prepared by the general formula The corresponding compounds of 1 are prepared by methods known per se, e.g., compounds of the general formula I of Chem. Water ratio? The backing can be prepared by reaction with 1 or 1 or 1% of the reaction mixture, ammonia or an amine (for example jetanolamine, triethanolamine, octylamine, morpholine or dioctylamine) in a suitable bath.

If desired, these salts may be made by recrystallization from two or more suitable bath salts.

The chemical salt of the general formula 1 is not only useful as a herbicidal activation compound in -'f:n et al.
The corresponding compound may be prepared using a solution of water or an organic solvent between a salt and a chemical compound, or by other techniques well known in the art. It can be used once again.

Compounds of formula V are prepared by methods known in the art, for example by reacting 2,3-fuchloro-5-trifluoromethylpyridine with hydrazine hydrate in ethanol. General formula V1. X11゜X seal, Xl
'M, Xff, XX,
XM, XXII, XXI.

xxxlX, xxxlv, XXXVI
VI) Compounds can also be produced by methods known per se.

2.3-Dichloro-5-trifluoromethylpyridine is a chemical compound as described in UK Patent Publication No. 2002368A.
It can be manufactured in many different ways.

The following Examples and Comparative Examples illustrate the preparation of compounds of general formula (1). Chromatography is performed using a silica column (
Merck & Co. 0.040-0.06.13+aR) 6.6
Row 1 at a pressure of N, m. c ivy.゛Ethoxymethylenemalononitrile [2,6Jl:f(uber, o
r, Amer, Chem, 'Soc,, 65th
Vol. 2224 (March 194) and 3-chloro-2-hydrazino-5-trifluoromethylpyridine (4,65
! 11) and glacial acetic acid (20 grams of sodium acetate (0)
, 917) at laboratory temperature. 2
A yellow solid precipitated from the dust, which was stirred for hours, and the resulting clear brown bath was dissolved at 15:11 after stirring.

This mixture was then filtered. The solids were washed with acetic acid, water, and water to give 3-chloro-5-trichloride having a melting point of 212-215°C. Fluoromethylpyrid-2-yl-hydrazinomethylene malononitrile (1.68 g) was obtained as a yellow solid.

The 3-diOk-5-trifluoromethylpyrid-2-yl-human2dinomethylenemalononitrile thus obtained was then diluted with 2
It was refluxed with heat for an hour.

This hot bath was passed through P, the P solution was cooled, diluted with water (100 d), and filtered to form a brown solid. Samurai, this is toluene (
50ml (1) and crystallized into 5 with a melting point of 199-200℃.
-amino-1-(3-chloro-5-trifluoromethylpyrid-2-yl)-4-cyanopyrazole (x, s8
g)' was obtained as a cream colored solid.

Stratified acetyl (0,95 mg) e1 chloroform (10
m1) Stirring suspension of 5-amino-1-(3-chloro-5-trifluoromethylpyrid-2-ylno-4-cyanopyrazole (prepared as described in Example 3, 1.07) of A)? ltl at 0°C.

Next, pyridine (0,56) in chloroform (5-)
A solution of m1) was added to the reaction mixture at 0-5°C. In the laboratory, the reaction product was heated once in the laboratory, and 1
I left it for the night. Dichloromethane (50
The mixture was diluted with water and washed with hydrochloric acid (2N: 50ml) and twice with water (2x50rd), dried over anhydrous hydroxide and evaporated to give a yellow solid. This solid silica column is used for chromatography.
After dichloromethane elution, the eluate was eluted with increasing acid ether (O~lO capacity%).The eluate containing the constituents transferred to rainbow oil was evaporated, and the melting point was 134-136.
Obtained 1-(3-chloro-5-trifluoromethylpyrid-2-yl)-4-cyano-5-diacetylaminopyrazole (o, 40 g) as a cream-colored solid.

Evaporate the eluate containing components that migrate slowly, and
5-acetamide-1-(3-chloro-
5-Trifluoromethylpyridol-2-yl)-4-cyanobininol (0,309) was obtained as a black solid.

5-Amino-1 in dry dioxane (25m)
-(3-chloro-5-trifluoromethylpyrido-2-
A mixture of (1,0 g)-4-cyanopyrazole (9) and aqueous sodium hydroxide (0,1'I7) was heated to reflux for 16 hours. The reaction mixture was cooled and Then, ethyl iodide (1,13 dJk, 7JO) reaction? [!, The mixture was heated under reflux F for 2 hours, and then 9 mouthfuls of ethyl iodide (l-) were added. The reaction mixture was kept at room temperature for 24 hours.
The mixture was kept roughly for 24 hours and then evaporated to dryness. The residue was dissolved in dichloromethane (25 tnl).

and water (25ml). The residue was washed with aqueous aqueous solution (2N: 25 yd), dehydrated with anhydrous sulfur, and evaporated to obtain a soybean residue.

This residue was applied to Chromadog 27 using 1 scoop of diethyl ether hexaben (1:2 cap) as a bathing agent. The bath solution containing 100 M of the product was evaporated and the melting point was 82-8.
1-(3-chloro-5-trifluoromethylpyrid-2-yl)-4-cyano-5-ethylaminopyrazole (0,17 g) at 4°C was polished with a mixture of diethyl ether and hexane. What did I do to you, who shattered you, as a roasted yellow body?

5-amino-1-(3-chloro-5-trifluoromethylpyrid-2-yl)-4-cyanovirazole (t
og, B: p-toluenesulfone brine, Fil product (0,
Heat for 1 hour with 0.02 lira: It was allowed to flow. The resulting reaction mixture was evaporated to dryness and the residue was chromatographed using dichloromethane as a gold plate.

The resulting eluate was evaporated to give a yellow semi-solid (O,
91 (l-m), which was recrystallized from a mixture of diethyl ether and hexane to give a melting point of 73-74 Cot-(3-
10 Rus-)! J fluoromethylpyridol 2-yl)
-4-Cyano-5-methoxymethyleneaminopyrazole (0,79) It appeared as a colorless solid.

5-amino-1- in chloroform (i amt)
(3-10-5-trifluoromethylpyridol-2-yl)-4-cyanopyrazole (1, (propionyl chloride (1,14)) was added to the stirring turbidity of IJ at 0°C. Then pyridine (0,
55ii+) The bath liquid was washed with NaI4; the mixture was stirred for 10 minutes and cooled to 0°C by external cooling.
The reaction mixture was stirred at 2C for 16 hours at room temperature, and the liquid was evaporated to dryness. The remaining W was removed by bathing in total ethanol (10+nl) and then aqueous ammonia (d = 0.1380
：l 01nl) and 7 intersections with salt.

The salt solution was reduced by heating for 3 hours and then evaporated to dryness. Distill the residue into chlormethane (100 g)
Dissolve in f, once with water, twice with 2N salt and twice with water? 511: Cleaned, dried over anhydrous magnesium chloride and evaporated. The thus prepared four-color bath solution is crystallized in toluene (lO) to give a melting point of iao ~ 132
1-(2-chloro-5-trifluoromethylpyrid-2-yl)-4-cyano-5-propionamidopyrazole (0.46 g) was layered and prepared as sand-like powder.

According to bRt Makoto Chino, is valeryl chloride substituted for propionyl chloride? ! The following compound was prepared by using 1 and adding ammonia to the reaction mixture and making it bulky with charcoal and kaliwam water: A mixture of toluene and hexane. 1- at 89-90°C.
(3-chloro-5-trifluoromethylpyrid-2-yl)-4-cyano-5-pentanamide pyrazole was obtained as a bright red solid.

5-amino-1 in dry chloroform (75ml)
-(3-chloro-5-trifluoromethylpyrido-2-
1jtt of yl)-4-cyanovidizole (5,07)
Half-evil to Shu-no-en, Kurorugi-no-enir (5,447)-
Added at 10°C. Pyridine (3,4
6)) The first meeting was held for 16 hours, during which time the reaction took place all at once. The reaction mixture was then cooled to -10°C and the chlorgylated phenyl (
Add 2,72g)'r and add bili gin (1,73')
j) added to '. The reaction mixture was stirred for an additional 16 hours at laboratory temperature.

The clear reaction mixture was evaporated to dryness and the residue was poured into diethyl ether (200ml). The liquor was purified with water (3 x 20 omit), dehydrated with Kakuba Natriwam, and evaporated to obtain a yellow oily solid, which was triturated with toluene (15 ml) to give a melting point of 191-193.
1-(3-chloro-5-trifluoromethylpyrid-2-yl)-4-7ano-5-di(phenoxycarbonyl)aminopyrazole (7.9 g)' was obtained as amber-colored cake crystals.

1-(a-chloro-5)lifluoromethylpyrido-2-
yl)-4-cyan-5-di(phenoxycarbonyl)
Aminopyrazole (prepared as described in Example 7);
z, 49) c-, 1,000 ml of sodium chloride in methanol was added to anhydrous methanol (prepared from sO-9) and the reaction mixture was Heat at reflux F for 1 hour.

The reaction mixture was evaporated to dryness and the residue was diluted with dichloromethane (150 d) and water (150 ml). The organic phase was separated, dissolved in water (2× to Oml) and anhydrous. Dehydration and evaporation over a magnesium hydroxide solution gave a yellow oil (1,4q), which was crystallized from a mixture of diethyl ether (5d) and hexane (15d) to give 4 points 128-129. 1-(3-chloro-5
-trifluoromethylpyrid-2-yl)-4-cyano-5-methoxylponylaminohyrizole (o, 5s
7) was observed as a colorless crystal.

According to my colleague Shijun, a similar product was prepared by using alcohol t1 instead of methanol; , melting point 11.9-120℃
1-(3-chloro-5-trifluoromethylpyrido-
2-yl)-4-cyano-5-ingloboxycarponylaminovirazole was obtained as colorless crystals.

Crystallized from a mixture of diethyl ether and hexane (1) with allyl alcohol, and chromatographed using dichloromethane-ethyl acetate (5:1 volume) as eluent. Melting point 105-10
1-(3-chloro-5-trifluoromethylpyrid-2-yl)-4-cyano-5-(2-7"robenyloxypolonylamino)pyrazole was obtained as colorless crystals at 6°C.

Dry acetonitrile (15ty)'f 5-amino-!
-(3-chloro-5-trinoorometervirido 2-
yl)-4-cyanobilanol (3,υ)) and 3-chloro-2-methylglobionyl clodiide (7,37)
The mixture was heated to calothermal reflux for 15 hours. The reaction mixture was evaporated under reduced pressure F to obtain a solid, which was treated with decolorizing charcoal and then recrystallized from toluene, with a melting point of 15.
1-152.5t4)l=lJ5-(3-chlor-2
-methylpropionamide)-1-(3-chloro-5-
Trifluoromethylpyrid-2-yl)-4-cyanopyrazole (t57J) was obtained as a pale yellow solid.

Example 8 - Preparation of products -1613, 7 and 8 5-(a-chloro-2-methylglopionamide)-i in a mixture of dimethylformamide (io,s) and dichloromethane (40ml) -(a-chloro-5-trifluoromethylpyrid-2-yl)-4-cyanopyrazole (1
, 4(1,), dimethylformamide (lOf
nt) and dichloromethane (40 grams of powdered sodium hydride (0,21)) was mixed with a mixture of 40 grams of powdered sodium hydride (0,21]), and then mixed with a mixture of dichloromethane and dichloromethane (0,21) for 1 hour at laboratory temperature. Then,
The reaction mixture was stirred for 2 hours. A saturated water bath solution of ammonium chloride was added to the reaction mixture at 77 Il'z, and the organic phase was removed, washed with water, dried over anhydrous sulfuric acid, and evaporated to dryness. The residue was chromatographed using a bathing agent of diethyl ether-hexane (1:2 volumes). ℃ tani (3-chloro-5-drifluoromethylpyrido 2-
yl)-4-cyano-5-(3-methyl-2-oxo-
azetidin-1-yl) pyrazole (0,33!7.l
' served as a colorless crystal.

In a similar manner, the following was prepared by modifying the analogous chloride of acetyl chloride.

After crystallization from a mixture of toluene and hexane, 1-(3-chloro-5-)! has a melting point of 165-166°C. jFluoromethylpyridol-2-yl]-4-cyano-5-cyclolacememidopyrazole t1 Obtained from dichloroacetyl chloride as a pale yellow solid.

After such crystallization, a mixture of toluene and hexane was obtained, 1-(3-chloro-5-trifluoromethylpyrid-2-ylcu-4-cyano-5-succinimide pyrazole tb Comparative Example 1 Starting from Example 3, one additional use was made; /C3-chloro-2-hydrazino-5-trifluoromethylpyridine was produced as follows: English@Patent Publication No. 2.002.368 A 2,3-dichloro-5-trifluoromethylpyridine (10.37g) described in No. 1 Homare was added to ethanol (50mt).
Hydrazine hydrate (99-100 w/w%; 7
．． 5d) and the mixture was heated to reflux for 24 hours. Next, what about the reaction mixture? The mixture was cooled, evaporated to dryness, and the remaining 'fIIvlJ was dissolved in ethane (
Recrystallization from 25ml of 3-chloro-2-hydrazinoni-5-to')fluoromethylpyridine (4,85(j) with a melting point of 88-90°C) was obtained as a gray solid. It was recrystallized from hexanoyl chloride as colorless crystals of 3-chloro-2-human-2-5-trifluoromethylpyridine with a melting point of 87°C.

The various formulas listed in the Unknown Honor are as follows: CF"/C R"NHNH* VH, ts HRa R"OHlX R1'l Ra R1" RAIL R3 R1lX1X! R” HR' RI I R1 HR” R” RJ g”R”COXVII Rsu0 R11X1XIl[ R”COX XX(R”Co
)*OXl R1”cox 朕(R”Co
) to XXI12 21 nxx on XXvIR”
COX XX [Rp-C=N- I
HOxxx～■ ■Continuation of page 231100 ) (C07D 401/14 207100 7242-4 C1
3100 231100) Priority claim January 11, 1984 [Ministry] United Kingdom (
GB)■8400690 0 Inventor: Edgar William Parnell, King of the United Kingdom, Sex Hornchurch, Emerson Park, Plutskside 10 0 Inventor: David Alan Roberts 78 Brickhill Drive, Betford, Bedfordshire, England

Claims (1)

[Claims] (1) General formula: [In the formula, R ~ (1) hydrogen atom, (tl)R,' c (-o)- group (where R4 is a hydrogen atom, 1 to 7 straight-chain or branched alkyl radicals having 1 to 4 carbon atoms; straight-chain or branched alkoxy radicals having 1 to 4 carbon atoms; or straight-chain or branched alkoxy radicals having 3 or 4 carbon atoms; Alkenyloxy group, alkyl and alkoxy groups within the definition of R4 are unsubstituted or straight-chain or branched alkoxy groups having 1 to 4 carbon atoms, 2 to 8 carbon atoms or B4 is a straight-chain or branched alkoxycarbonyl group having 3 to 6 carbon atoms, which may be substituted by one or more halogen atoms, or B4 is unsubstituted or substituted by a methyl or ethyl group. (1 pupil group R5 (where R5 is a straight-chain or branched alkyl group having 1 to 8 carbon atoms or 2 to 8 represents a straight-chain or branched alkenyl or alkynyl group having 5 carbon atoms, and the alkyl, alkenyl and alkynyl group represented by R5 may be unsubstituted or a cyano group,
Hydroxy group, straight-chain or branched alkoxy group having 1 to 6 carbon atoms, carboxy group, straight-chain or branched alkoxycarbonyl group having 2 to 9 carbon atoms, aminocarbonyl group (this is 1 even if unsubstituted
optionally substituted by one or two straight-chain or branched alkyl groups having ~8 carbon atoms,
When the aminocarbonyl group is substituted with two alkyl groups, these may be the same or different, or two to two alkyl groups may be substituted.
optionally substituted by one or two straight-chain or branched alkenyl or alkynyl groups having 8 carbon atoms; if the aminocarbonyl group is substituted by two alkenyl or alkynyl groups; These may be the same or different), the alkoxy moiety is 1-
an alkoxyaminocarbonyl group having 8 carbon atoms and which may be linear or branched; an alkanesulfonamidocarbonyl group in which the alkane moiety has 1 to 8 carbon atoms and which may be linear or branched; -C(=O)Het group, where Het has 3 to 7 atoms in the ring with up to 2 additional heteroatoms selected from oxygen, nitrogen and sulfur and R5 is unsubstituted or 1~
3 to 6 substituted by one or more straight-chain or branched lower alkyl groups having 4 carbon atoms
represents a cycloalkyl group having 1 carbon atoms), R2 is a hydrogen atom when (1) R'' represents a hydrogen atom, (1) R1 represents an R'C(-0)- group (wherein R4 has the above meaning), hydrogen atom or R4C(-
o) - group (when shown here, hydrogen atom or the above R
5, or R1 and R2 taken together -Co-(CR"Rb). -CO- (where ReL and Rb may be the same or different (, each hydrogen atom or a straight-chain or branched alkyl group having 1 to 4 carbon atoms, m is 2
or 3), or R1 and R2 together with the nitrogen atom to which they are bonded represent the general formula: represents a straight-chain or branched alkyl group having 6 carbon atoms, n represents 0.1 or 2, n represents 1
or 2, the moiety -C in the group of the above general formula (■)
(R')C(-Rd))- and -CCRo-)CC-
Rd)]2-, B0 and Hcl may be the same or different), or R1 is a group in which the alkyl moiety is 1 to 4
represents an alkylthio group having 5 carbon atoms and which may be straight or branched, and R'' represents a hydrogen atom, or R
I and R2 together with the nitrogen atom to which they are attached represent a group of the general formula: where Hp is a straight or branched alkynyl group having 1 to 4 carbon atoms or each 1-4
refers to an amino group substituted by one or two straight-chain or branched alkyl groups having 5 carbon atoms, and when an amino group is substituted by two alkyl groups, these may be the same or different. HQ may be a hydrogen atom or 1
N-pyridylpyrazole derivatives of the following formula: a straight-chain or branched alkyl group having ~4 carbon atoms, R3 represents a group of the general formula: where R6 represents a chlorine atom; In the case of an alkyl, alkenyl or alkynyl group substituted by a group, its salt with an agriculturally acceptable base. +2+ R," represents an R'C(-0)- group, R4 is a straight chain or branched alkyl group having 1 to 7 carbon atoms or a straight chain having 1 to 4 carbon atoms or a branched alkoxy group, which may be substituted by one or more chlorine atoms (and in which R2 and R3 have the meaning given in claim 1) N-pyridylpyrazole derivatives according to paragraph 1. Indicates a straight-chain or branched alkenyl or alkynyl group, which may be unsubstituted or substituted as defined in claim 1 (and R2 and R3 are N-pyridylpyrazole derivatives according to claim 1 having the meaning defined in claim 1. a branched alkyl group or a straight-chain or branched alkenyl or alkynyl group having 2 to 8 carbon atoms, substituted by one or more chlorine atoms, and R2
The N-pyridylpyrazole derivative according to claim 1, in which R3 and R3 have the meanings defined in claim 1. (5) R1 represents a group R5Y, and R5 is a linear or branched alkyl group having 1 to 4 carbon atoms or 2 to
Claim 1 represents a straight-chain or branched alkenyl or alkynyl group having 4 carbon atoms, which is unsubstituted or substituted as defined in claim 1 or claim 4. The N-pyridylpyrazole derivative described in . (6) 5-amino-4-cyano-1-(3-chloro-5
-trifluoromethylpyrid-2-yl)pyrazole,
1-(3-ri4-5-trifluoromethylpyrido-2
-yl)-4-cyano-5-diacetylaminopyrazole. 5-acetamido-1-(3-chloro-5-trifluoromethylpyrid-2-yl)-4-cyanopyrazole, 1
-(3-chloro-5-trifluoromethylpyrido-2-
yl)-4-cyano-5-ethylaminopyrazole, 1
-(3-chloro-5-trifluoromethylpyrido-2-
yl)-4-cyano-5-methoxymethyleneaminopyrazole, 1-(3-chloro/l/-5-)lifluoromethylpyrid-2-yl)-4-cyano-5-propionamidopyrazole, 1- (3-chloro-5-trifluoromethylpyrid-2-yl)-4-cyano-5-dichloroacetamidopyrazole, 1-(3-chloro-5-trifluoromethylpyrid-2-yl)- 4-cyano-5-succinimidopyrazole, 1-(3-chloro-5-trifluoromethylpyrid-2-yl)-4-cyano-5-
'; (phenoxycarbonyl)aminopyrazole, 1
-(3-chloro-5-trifluoromethylpyrido-2-
yl)-4-cyano-5-impropoxycarbonylaminopyrazole, 1-(3-chloro-5-trifluoromethylpyrid-2-yl)-4-cyano-5-methoxycarbonylaminopyrazole, 5-( 3-ri stomach roux 2-
methylpropionamide)-1-(3-chloro-5-trifluoromethylpyrid-2-yl)-4-cyanopyrazole, 1-(3-chloro-5-trifluoromethylpyrid-2-yl)- 4-cyano-5-(3-methyl-2
-oxo-azetidin-1-yl)pyrazole, i -
(3-chloro-5-trifluoromethylpyrid-2-yl)-4-cyano-5-(2-propenyloxycarbonylamino)pyrazole, and 1-(3-chloro-5
The N-pyridylpyrazole visiting conductor according to claim 1, which is -IJfluoromethylpyrido2-I#)-4-cyano-5-pentanamidopyrazole. t71! When AlR1 and R2 each represent a hydrogen atom and R3 has the meaning described in claim 1, the compound of formula 2 [wherein R3 has the meaning described in claim 1] cyclization, ini R,'' and B2 each represent a hydrogen atom and R3 has the meaning described in claim 1, the formula: % formula % [wherein R3 is defined in claim 1] A compound of the general formula: %C in which R7 represents a straight-chain or branched alkyl group having 1 to 4 carbon atoms] is reacted with a compound of the general formula: , [CI R'' represents a R''C(=O)- group, R8 has a meaning other than the hydrogen atom indicated for B4 in claim 1, and R2 is a hydrogen atom or R2O(= O
)-group Z, R8 has the above meaning and is the same as the group R8C(-0)- represented by R1, and R3 has the meaning described in claim 1, A compound of the formula R3 [wherein R3 has the meaning described in claim 1] or an alkali metal derivative thereof is represented by the general formula: %Formula% [wherein, X represents a chlorine or bromine atom, and R8 has the above-mentioned meaning] or with a compound of the general formula: % formula % [wherein R8 has the above-mentioned meaning] to react with a compound of the formula: L,,R4e
L represents a hydrogen atom, R2 represents a hydrogen atom, and R3
dog ≠ -41 eyes 4 paA chyme chi-1 disease If it has the meaning described in claim 1,
(where R3 has the meaning given in claim 1) is reacted with formic acid. +E+R1kaR"c (=o)--group L, R4a
starts a hydrogen atom, R2 is a hydrogen atom or R4aC (=
O)- group, R" represents a water- A compound having the meaning described in Range 1) is reacted with formyl acetic anhydride, (FI FI '' represents an R4c (-〇)- group, FI
4 has the meaning described in claim 1, R2 represents a hydrogen atom, and R3 has the meaning described in claim 1, the general formula shown in claim 1
(Here, R1 and R2 are respectively P, 'C(=O)-
group, R3 and R4 have the above-mentioned meanings). 'C(=O)- is selectively removed by hydrolysis under mild conditions f-1 to convert it into one Z hydrogen atom, and IGI R'' is converted into R'bC(-0)-base and R4b represents a linear or branched alkoxy group having 1 to 4 carbon atoms as shown for R4 in claim 1, R2 represents a hydrogen atom, and R3 represents a If it has the meaning given in paragraph 1, the general formula: [wherein R15 represents a group R16C(-0)-, R16 is an unsubstituted or alkoxy group having 1 to 4 carbon atoms] , represents an alkoxycarbonyl group having 2 to 8 carbon atoms or a straight-chain or branched alkoxy group having 1 to 4 carbon atoms substituted by one or more halogen atoms, and R phenoxy group] is reacted with a compound of the general formula; substituted, R15 is a group R”C(-0)-
(Here, R16 represents a phenoxy group), the other group represented by the symbol RIS is substituted with R''C(=O)- (wherein R14 has the above meaning), and the desired Then, if R15 represents the group R16c (=o) - (here, R16 represents the group defined in R14), then R
Other groups represented by 11i are replaced by other groups R”C(-0)-
(6) R2 represents R'C(-0)-, R4 has the meaning described in claim 1, and R2 represents R'C(=O
)- group, R4 has the meaning described in claim 1, and may be the same or different from the R' C(=O)- group represented by R1 (and R3 has the meaning described in claim 1). range 1
If it has the meaning described in the section, the general formula: [wherein R12
represents a group R'C(-0)-, where R4 has the meaning defined in claim 1, and R3 has the meaning defined in claim 1. The alkali metal derivative is represented by the general formula (2) in formic acid, formyl acetic anhydride or IcI (where R8 and
has the meaning shown in icl), and (IIR' and R2 together form -C0-(CI:l
aRb)m-Co-, where H&, Hl) and m have the meaning given in claim 1, and R
3 has the meaning stated in claim 1,
The compound of IA shown in CI (where R3 has the meaning described in claim 1) is prepared by the general formula: and X has the meaning given in CI] or a compound of general formula 2 [wherein Ra, Rb and m have the meanings given in claim 1] (J) B'' represents a group R5Y, where R5 has the meaning as defined in claim 1, and R2 is a hydrogen atom or as defined in R5 as defined in claim 1. Indicates the group,
And when R3 has the meaning described in claim 1, the general formula: [wherein R17 represents a hydrogen atom or a group defined as R5 described in claim 1, R5 represents a straight-chain or branched alkyl group having ~4 carbon atoms
has the meaning given in claim 1] with a compound of the general formula V shown below (wherein R3 has the meaning given in claim 1), (Transition) R1 represents a group R5, where R5 has the meaning described in claim 1, and R3 represents the group R5 in claim 1.
has the meaning described in the section, and R2 is a hydrogen atom or the symbol R
When the group R5 is the same as the group R5 shown in 1, the compound of the formula (1) shown in CI (where R3 has the meaning described in claim 1) or its alkali metal derivative, 1 or 2 molar proportion of a compound of the general formula: ゛R5X'' fL) A group R5 in which B'' is a group R1llR19CH-
where R18 and Rj9 together with the carbon atom to which they are bonded have 1 to 8 carbon atoms and are unsubstituted or 77 groups, hydroxy group, 1 to 8 carbon atoms;
Straight-chain or branched alkoxy groups with 6 carbon atoms, carboxy groups, straight-chain or branched alkoxycarbonyl groups with 2 to 9 carbon atoms or one or more carbon atoms represents a linear or branched alkyl group substituted by, and R2 represents a hydrogen atom and R3 has the meaning described in claim 1, the general formula: [wherein R3 is having the meaning given in claim 1, and R18 and R19 having the above meanings], R1 represents group B5, where R5 is If R2 represents a hydrogen atom and R3 has the meaning described in claim 1, the general formula: [wherein R3 and R' are The group R"Co- of a compound having the meaning as defined in claim 1, and R represents a straight-chain or branched alkyl or alkoxy group having 1 to 4 carbon atoms is removed. , (f) When IRI and R2 each represent a methyl group and R3 has the meaning described in claim 1, formula IA shown in (C) (where R is 1) is reacted with formic acid in the presence of acetic acid, (o) represents a group B5 in which R' is a group CH2R21,
R is an unsubstituted group having 1 to 7 secondary atoms, or a cyan group, a hydroxy group, a straight-chain or branched alkoxy group having 1 to 6 carbon atoms, or one or more In the case where R2 represents a hydrogen atom and R3 has the meaning described in claim 1, the general formula: , R3 and R21 have the above meanings], (P) the group R5 represented by R1 has an alkoxycarbonyl substituent having 2 to 9 carbon atoms, and When R2 represents a hydrogen atom or a group R5 which may have an alkoxycarbonyl substituent having 2 to 9 carbon atoms, the name of the alkoxycarbonyl substituent of the compound within the definitions given above is 1 to 8. carbon atoms and the alkoxy moiety is transesterified with an alkanol different from both alkoxy moieties of the group R5 represented by R1 and R2, When R2 has a carbonyl substituent and R2 represents a group R5 which may have a hydrogen atom or an alkoxycarbonyl substituent having 2 to 9 carbon atoms, the 2I shown in claim 1 (Here, the group R5 represented by R1 has a carboxy substituent, R2 represents a hydrogen atom or a group R5 which may have a carboxy substituent, and R3 has the meaning described in Claims No. esterification of the corresponding compound (having) with an alkanol having 1 to 8 carbon atoms, +1'UR'' represents a group R5, where R5 is a straight-chain or branched group having 1 to 8 carbon atoms. Indicates a chain alkyl group or an alkenyl or alkynyl group having 2 to 8 carbon atoms and substituted as defined in claim 1, with the exception that cyano, hydroxy, 1 to 6 carbon atoms A straight chain or branched chain alkoxy group having an atom, a carboxy group and one or more halogen atoms are excluded, and R2 represents a hydrogen atom and R3 has the meaning described in claim 1. is a general formula: [wherein R3 has the meaning as described in claim 1, and Br is a linear or branched alkylene group having 1 to 8 carbon atoms or 2 to 8 represents a straight-chain or branched alkenylene or alkynylene group having 1 to 8 carbon atoms]. alkoxy groups in the chain, amine groups which are unsubstituted or substituted with one or two straight-chain or branched alkyl groups having 1 to 8 carbon atoms (an alkyl group in which the amino group has two the alkyl substituents may be the same or different) or by one or two straight-chain or branched alknyl or alkynyl groups having 2 to 8 carbon atoms. an amino group (where the amine group is substituted with two alkenyl or alkynyl groups, these may be the same or different), an alkoxy moiety having 1 to 8 carbon atoms and a straight chain; an alkoxyamino group which may be straight-chain or branched, an alkanesulfonamide group in which the alkane moiety has 1 to 8 carbon atoms and which may be straight-chain or branched; Reacting with the compound (representing a Het group described in Range 1) or, when R24 represents an alkanesulfonamide group, with an alkali metal salt of an alkanesulfonamide represented by the general formula XXXrv, and (SIR" is a group R5 , where R5 has 1 to 8 carbon atoms and is an alkane sulfonamidocarbonyl group (wherein the alkane moiety has 1 to 8 carbon atoms and is linear or branched). ), R2 represents a hydrogen atom, and R3 has the meaning described in claim 1, the claims General formula I (
Here, R1 represents a group R5, R5 is a straight or branched alkyl group having 1 to 8 carbon atoms and substituted with an unsubstituted aminocarbonyl group, or a straight chain or branched alkyl group having 2 to 8 carbon atoms. represents a straight-chain or branched alkenyl or alkynyl group substituted with an unsubstituted aminocarbonyl group, R2 represents a hydrogen atom, and R3 has the meaning given in claim 1. ) is reacted with alkanesulfonyl chloride (wherein the alkane moiety has 1 to 8 carbon atoms and may be straight or branched), and (T) R1 is a straight-chain or branched alkyl group having 2 to 8 carbon atoms and substituted by a hydroxy group, or a straight-chain or branched alkyl group having 3 to 8 carbon atoms and substituted by a hydroxy group; represents a straight-chain or branched alkenyl or alkynyl group substituted by R2
represents a hydrogen atom and R3 has the meaning described in claim 1, the general formula 2 [wherein R3 has the meaning described in claim 1],
P,' represents a straight-chain or branched achilene group having 1 to 7 carbon atoms, or represents a straight-chain or molecular chain alkenylene or alkynylene group having 2 to 7 carbon atoms, and Rlj is represents a hydrogen atom or a straight-chain or branched alkyl group having 1 to 8 carbon atoms, and T
1 represents a hydrogen atom, or when Hu represents an alkyl group, it can also represent a ksT1kt group R25(C-0)-, where R25 is a straight or molecular chain having 1 to 41 carbon atoms. represents an alkyl or alkoxy group] and (UIRl represents a group R', where R5 has 1 to 8 carbon atoms and is substituted by a chlorine atom). A straight-chain or branched alkyl group or a straight-chain or branched alkenyl or alkynyl group having 2 to 8 carbon atoms and substituted by a chlorine atom), R2 represents a hydrogen atom, and R
3 has the meaning stated in claim 1,
General formula I according to claim 1 (where R1 is 1
a straight-chain or branched alkyl group having ~8 carbon atoms and substituted by a hydroxy group, or a straight-chain or branched chain having from 2 to 8 carbon atoms and substituted by a hydroxy group represents an alkenyl or alkynyl group, R2 represents a hydrogen atom and R3 has the meaning given in claim 1) is reacted with thionyl chloride, (VIR'' represents a group R5, where R5 represents an alkylthio group, the alkyl portion of which has 1 to 4 carbon atoms and may be linear or branched (where R2 represents a hydrogen atom and R3 represents a claim) If the meaning given in claim 1 is given, the alkali metal salt of the compound of formula IA shown in C1 (wherein R3 has the meaning given in claim 1) is added to an alkanesulfenyl chloride (wherein the alkane sulfenyl chloride is (the moieties have 1 to 4 carbon atoms and may be straight or branched), @R and R together with the nitrogen atoms to which they are attached The general formula xxxn (herein R1) described in claim 1 represents a straight or branched alkoxy group having 1 to 4 carbon atoms, and R
Q represents a group having the meaning given in claim 1), and when R3 has the meaning given in claim 1, means the compound defined in claim 1),
General formula: 2R"-C(OR"") a represents a straight-chain or molecular-chain alkyl group having 5 carbon atoms; α) R and R are combined with the nitrogen atoms to which they are bonded; General formula xxxn (
Here, R1) each has 1 to 4 carbon atoms and represents an amino group substituted with one or two straight-chain or branched alkyl groups, which may be the same or different; (Rq has the meaning set forth in claim 1); and when R3 has the meaning set forth in claim 1, the general formula I set forth in claim 1 (Here, R1 and R2 together with the nitrogen atom to which they are bonded represent a group of the general formula xxxn described in claim 1, where Rp has 1 to 4 carbon atoms. Rq has the meaning described in claim 1, and R3
has the meaning given in claim 1), wherein the alkyl moieties each have from 1 to 4 carbon atoms and can be linear or branched. (YIR" represents a group R5, where R5 is a group of 2 to 8 Contains a carbon atom and is unsubstituted or has an α position of 1 to 6
represents a straight-chain or branched-chain alkyl group substituted with a straight-chain or branched-chain alkoxy group having 5 carbon atoms, R2 represents a hydrogen atom, and R3 represents the If it has a meaning, the general formula 2 [wherein R3 has the meaning described in claim 1, and RY is a hydrogen atom or a straight or branched chain having 1 to 7 carbon atoms] an alkyl group, and T2 represents a hydrogen atom or a linear or branched alkoxy group having 1 to 6 carbon atoms]. fZI R" represents a group R5, in which R5 is a straight-chain or branched alkyl group having 2 to B carbon atoms and substituted by a carboxy group, a straight-chain alkyl group having 2 to 9 carbon atoms; a chain or branched alkoxycarbonyl group, or an amino substituted with one or two straight-chain or branched alkyl groups, each having from 1 to 8 carbon atoms; Indicates a carbonyl group, and when the aminocarbonyl group is substituted with two alkyl groups, these may be the same or different (or one
refers to an aminocarbonyl group substituted with two or two linear or branched alkenyl or alkynyl groups each having 2 to 8 carbon atoms, where the aminocarbonyl group is substituted with two alkenyl or alkynyl groups; (If R2 represents a hydrogen atom and R3 has the meaning set forth in claim 1, then the general formula (Here, R1 and R2 together with the nitrogen atom to which they are bonded represent a group of the general formula (2) described in claim 1, where Re. Rd, R'', Rf, Rg , Rh and n have the meanings described in claim 1, provided that the group of general formula (1) has 2 to 8 carbon atoms excluding the carbon atom of the carbonyl group, and B3 has the meaning as described in claim 1. range (having the meaning described in item 1)), in order to cleave the amide group of the general formula straight-chain or branched alkanols or ammonia or mono- or di-chain carbon atoms having
Alkylamines (wherein the alkyl moieties may be straight or branched and each have from 1 to 8 carbon atoms and may be the same or different in the case of dialkylamines) or mono - or a di-alkenyl or alkynylamine (wherein the alkenyl or alkynyl moiety may be straight or branched (and each having 2 to 8 carbon atoms) may be the same or different in the case of (herein, HC, Bd, Be; Rf, R, g, Rh and n have the meanings set forth in claim 1), and R3 represents the group set forth in claim 1. If it has a meaning, the general formula: ] of the general formula (2) according to claim 1, characterized in that the compound is treated with a base (wherein R', R
2 and B3 have the meanings given in claim 1). (8) % Allowable range General formula I according to claim 1 (where B
One or each of the groups represented by 1 and R2 has a carboxy substituent, and R3 is
8. The method according to claim 7, further comprising the step of converting the N-pyridyl pyrazole derivative (having the meaning given in claim 7) with a salt thereof using an agriculturally acceptable base in a conventional manner. (9) General formula (■) according to claim 1, produced by the method according to claim 7 or 8
(wherein R1, R2 and R3 have the meanings given in claim 1) or a suitable salt with an agriculturally acceptable base. aI The general formula described in claim 1 as an active ingredient! (where n i , R2 and R3 have the meanings given in claim 1) of one or more suitable herbicidally acceptable N-pyridylpyrazole derivatives. A herbicidal composition containing a diluent or a carrier and/or a surfactant.The herbicidal composition according to claim 10, which contains an N-pyridyl bisizole derivative having an α110.05 to 90 weight ratio. The herbicidal composition according to claim 10 or 11, which contains α21 or more other insecticidal (including herbicidal) compounds. General formula ■ (here B1
, R2 and lll3 have the meanings set forth in claim 1). A method for suppressing weed growth in a habitat, the method comprising applying a composition to the habitat. Q4) 3-chloro-5-trifluoromethylpyrid-2-ylhydrazinomethylene malononitrile. A compound of general formula I according to claim 1, in which Q51'r3'B2N-ka represents an open-chain alkenylcarbonylamino group, and R3 has the meaning defined in claim 1. Oe A compound of the general formula: n has the meaning given in claim 1, and R3 has the meaning given in claim 1. αη General formula: [In the formula, Ro, R', R", Rf, Rh and n have the meanings described in claim 1, and R and R.
1 may be the same or different XXX 9 ・Each represents a hydrogen atom or a linear or branched alkyl group having 1 to 3 carbon atoms, and the total number of carbon atoms in Rk and P ・1 is 3 or less, and R3 has the meaning given in claim 1.