JPS5967293A - Phosphorus-containing functional group derivatives of aceticacid, manufacture and herbicide and plant growth regulant - 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] Japanese Patent Application No. 54-89027 discloses the formula (HO), P
Phosphonoglycine represented by (0)OH(NH,)OOOHte is described as a compound having herbicidal properties.

The present inventors have now discovered that numerous (14) other phosphorus-containing functional group derivatives of acetic acid have excellent herbicidal and plant growth regulating properties.

The subject of the present invention is the general formula (in which R1 and R1 are independently of each other (Os-01o)-alkyl, O'F3.benzyl, cyclohexyl, cyR8
is -OH, SH, (Cr -Crt ) -7k koxy, (C3-C,)-cycloalkoxy, (CsC'a
)-alkenyloxy, (Cs'a)-alkynyloxy, phenoxy or benzyloxy, which groups are themselves substituted with OH, halogen, OF, (C1-04)-alkyl or (0104)-alkoxy; (c+as)-alkylthio, (asa,)
-cycloalkylthio, (C.

(15) 10,)-alkenylthio, (C3-06)-alkynylthio, phenylthio or benzylthio (these groups are themselves halogens, OF, (01=04)-alkyl or (0,-0,) -alkoxy); amino, (at 04)-alkylamino, hydroxylamino, O-(al-C,)-alkylhydroxylamino, di(C1-C,)-alkylamino, anilinos (C1'+.)-Phenylalkylamino, di(Cy -0H(1) -yenylalkylamino, N-phenyl-N-(C, -0,)-
alkylamino, N-phenyl-N(C3-06)-alkenylamino- or N-phenyl-N-(Csea
)-alkynylamino (these groups themselves are OH, halogen, (C,-04)-alkyl-spanning (0104)
- may be substituted with alkoxy); hydrazino,
β-(CI-04)-alkylhydrazino, β, β-di(CI-04)-alkylhydrazino, piperidino,
Pyrrolidino, morpholino, 2,6-dimetermorpholino (
R4 means (Ot's)-alkyl, allyl, bronoclyl, benzyl or norogenpenzyl; R6 and R6 independently of each other represent hydrogen, (C+ 'tt)
-alkyl, (Osa,)-cycloalkyl, (O
sOa)-alkenyl, (('s'a)-alkynyl,
Phenyl, benzyl, benzoyl, phenoxysulfonyl, (Cs-Crt)-alkylsulfonyl, (C
s-Ce)-alkenylsulfonyl or t is phenylsulfonyl (these groups themselves), rogene, OF3, C
N, (CI-04)-alkoxy (C1-C4)
- optionally substituted with alkoxycarbonyl); R1 is hydrogen, (C1-06)-alkyl, (C2C,)
-alkenyl, (03o, )-alkynyl, (Ct(
17) -04) -Acyl, meaning halogen-(a, -a, )-acyl or benzoyl; R1 and R, independently of each other mean (CI-Crt)-alkyl or together 3 to 8 (meaning an alkylene group having 0 carbon atoms) and their salts with bases or acids (provided that when R1 and R7 and A is a group represented by the formula 0 formula % ( ), at the same time - It is never OH).

In the above, "Haz" or "1 halogen" preferably means chlorine or bromine. The skin aliphatic groups mentioned for R8 are preferably hydroxy, (CI'4) insofar as they are substituted. - mono-substituted by alkoxy or halogen, especially chlorine.Aromatic groups are preferably substituted by halogen, especially chlorine, OF3, (01
-c, )-alkyl may be mono- or tri-substituted by (C, -a, )-alkoxy.

If the group R1+ - of R1 and R8 means -OH, or if R3 means 10H, then the compound of formula I can be used for inorganic and organic 2+ Ou, Fe2+ , N1! +, (atc'+)-alkyl-NH3''l-(0104)-alkyl-NU
, +, tree (0, -04) + one alcohol NH or (HOOT (,0H2), N
H+ is used.

When A represents the group -0H-NH, the compound of formula (1) may form salts with inorganic or organic acids having a dissociation constant >10''. ua4HBr or H2S
Strong mineral acids such as O, are particularly suitable for salt formation.

For example, the following groups are suitable as R1 to R and: T<1. R,,:OH3,O,H,,O,H,,OH3
,OH,ONa,OK.

ONE,;R,:OT(,0IJH,,ONa,OK,QC!H5
,00,H,,OOH.

OH, Ot , 00 H, OH, O) 1 , 00.
T(, (n), 0OH20HOzOH, OL, OCH,
OH, OH, CH, OH, 0CH2OF, , OCR,
Oh.

(19) 00H3,OCH,(1!H==OH,,ocH,c=
cu, oc, H,, oa, H.

C1cp)To" 6H4CH3(p), 00.'H3
0z, (o tT'), ocn2C,T(lI,O(
! H2C6H,OH, (p), cyclohexyloxy.

Cyclopentyloxy; S) I, SC, T(s, 5C
H20H==OH,.

So, H,; NH+4. NHCT(8,N'HO,H,
(n), NHCH2N(C'H,)t, N(0,H
,), ,NTTOH,NHCH20N(i-0,u,
)2. NHO,H,,NH-0,H,0z(p),N
H-0, H40H, (p), NHCH20, H,, N
Tl0FI, O)I, 06H,,N(OT(,)0
61T, ,N(OH,)06T(,Br,NH-0
,H,0CR3(p) ,NHNH,.

NU)THOH,, NUN(0,H,),;0N=O(
OH3).

A; 0HOO,H,,0H00,H7(i),
f:! HOOH,0H=OH,,0HOOH,C=(!
)(,auocH,-c,H,0L(p),CHOOH
,06H504(o,p'),0HOOH,O,H,B
r(p),0HOOONH,,0HOOOIJHOH,
,0H00ON(OH,)2,0HOOONH8O,O
H.

0HOOOIJHEIO,OH,0=OHOH,,0H
OOON(CH, CH=CH,)t.

0H200ONHO6H,,0R(lz,0HBr,O
'HNE,! ,01(NHO,H.

(n),C)IN(0,HII),,0HNH(!HO
,0TINHOOOH8゜0HNHOOCF, 6 The object of the present invention is also to prepare compounds of the general formula I (20) (a) In order to prepare compounds in which L means -C=o, formula 1 ( In the above formula, R1' and RI mean (Ct-C+o)-alkoxy or have one of the meanings of R1 and R1 (excluding OH)). (b) Ad-11,HOH'j,-Island,8. In order to produce a compound of the formula (21) (in the above formula, R7 and R,I mean (0+ -C+o')-alkoxy or each of R1 and R7). %() (wherein, X means =0, =NH49 means ==N-R, o, and R1° is benzyl, benzhydryl, trityl, ”C.C.
C1-0s)alkyl), -NEC,H, or-
NIIlooO(0,-04)alkyl) and optionally cleavage of the group R1° present by hydrogenolysis or hydrolysis; or (Q) obtained according to (b). A compound of the formula I is converted into another compound of the formula I by alkylation, no-logenation, benzylation, oxidation, acylation or amidation (22) and optionally R7 Alternatively, there is a method for producing a compound represented by the above formula I, which comprises hydrolyzing the alkoxy group present at the 4-position and converting a certain silicic acid into its salt.

Regarding (a): Are the starting materials of the formulas ■ and ■ known from the literature?
Volume 1, pages 208 and 324 and Volume I/2, page 53 (
Houben-Weyl, Methodenaer
org+Ohemie, Vol, ■/1.208.52
4, ■O1゜■/2.53)) or a similar method. The reaction with compound W is from 20° to 100"0
It can be carried out with or without addition of a solvent at a temperature of .

(23) Concerning (b): Are the starting materials of formula V known as well?
1) See Vol. Some of the compounds represented by formula (1) are known (Houben-Weyl).

Vol, ■, 217.280; Ber, 57. ! +1
90 (1904); Ann, 690, 158 (19
65)) or by a corresponding method. group R7
For the hydrogenolytic cleavage of 20°, hydrogen in the presence of palladium on charcoal is used as a catalyst (for example, Synthesis (19'80, 10).
28-32).

The solvent is the same as in (a), but with the addition of acetate ester, and the reactant IW is from 0 to 100'O, preferably from 10 to 30'O. In some cases it may be advantageous to accelerate the reaction by adding a base, such as NaO'H, KOHoNa
Alkali metal hydroxides or alcoholates such as ooT (and 0-tert-butyl) or tertiary phosphorus bases such as triethylamine or methyldi(24)isopropylamine are preferred.

Regarding (c): The compound of the formula (3) in which X represents oxygen can be prepared by using an incyanate represented by the formula R, -LN=O=O or a chloroformylamine represented by the formula R,R,N-000t. is converted into the target product of formula I with input=-OR0OONR,R, in a manner known in the art, when inocyanate is used.
f, R5 is H. Pat.

Pat8. When using a /% rogenating agent such as PBr3 and 5ocz, the corresponding /% rogen compound (A--cHuaz) is obtained from ■. Kowara no 7・
The rogen compounds can be further converted into the corresponding amino compounds (A=-OHN
H,). Alkylation, acylation or benzylation at the group -XH, A=-CHO(c, -c,
)alkyl, -aHo ()-logen)benzyl or -HNT (R, (where R, %'H). For example, from ■(x-0) by oxidation with chromium mitaki It is also possible to obtain compounds of the formula I in which A=CO (25).

All stiff reactions are well known to those skilled in the art and no further detailed explanation is necessary.

As is clear from the formula (2), an asymmetric center is created by adding the phosphorus compound V to the compound represented by the formula (2). The compounds of formula 1 can therefore exist as optically sensitive forms, which are likewise a subject of the invention.

The compounds according to the invention exhibit an outstanding and extremely widespread herbicidal action against a wide variety of annual and perennial grass weeds and broad-leaved weeds on roadsides, industrial sites or railway sites. have The subject of the invention is therefore also herbicides and plant growth regulators containing compounds of the formula I and used for controlling undesired plant growth.

The active substances according to the invention are suitable for use in weed control in horticulture and elsewhere. They may be used on annual or perennial crops as long as the method of application and/or growth stage of the straddle crop (26) ensures that the cultivated plants and their sensitive green parts are not damaged. can do. Examples of such possible applications are use in farms, plantations, vineyards, etc.

Since the application of the novel compounds according to the invention before the germination of cultivated plants causes no or very little damage to these plants, they can be used for the control of weeds before the germination of the seeds, before sowing or even after harvesting. be able to,.

However, the compounds according to the invention can also be used in cultivated plants (
It can also be used to control the growth of the cotton or potato plant itself, for example, if the growth impedes harvesting.

The novel compounds according to the invention are used. Depending on its purpose, typical growth-regulating effects can thereby also be achieved, and thus, for example, the growth of plants as well as the desired physical performance of plants can be influenced. Therefore, the compounds of (27) and straw are suitable as growth regulators of useful plants such as cereals, corn, sugar beet, tobacco, rice and turgid.

On the other hand, it can also be used, for example, for the conditioning of lawns, shrubbery, roadsides and ornamental plants.

Plant growth of a large number of monocotyledonous and dicotyledonous plants is suppressed by application of the compounds according to the invention and, as a result, inter alia, the carbohydrate content in the plants or in their fruits is increased. As a result, the Xi-K of desirable plant contents, such as carbohydrate proteins or carbohydrates (starch, sugar), has a positive influence.

For example, the sucrose content of sugar cane and sugar beets increases, and the fructose content of fruits and grapes increases710
Suru. In other plants such as potatoes, corn, turgids and grasses (clover and lucerne) the total starch increases. The benefits thereby achieved are obvious and therefore require no further explanation.

(28) Applications are made approximately one week to five months before harvest. At the end of this period, the degree of yield by the active substance, ie the carbohydrate anastomosis d, reaches a maximum. It should be remembered that, in general, the growth rate and flourishing period of crops can vary over a fairly wide range. For example, sugarcane grows between 1 and 3 times per year depending on its growing location and climate.
It takes years. The timing of application should also be changed to picking according to Senna. In the case of sugar beets, this may be, for example, 1 to 13 weeks before harvest.

The agent according to the invention includes wettable powders, emulsions, spray solutions, powders,
It is used in the usual formulation form as a dipping agent, dispersion, granule or microgranule.

Wettable powders are preparations which can be uniformly dispersed in water and which contain, in addition to the active substance, optionally further diluents or inert homogeneous, wetting agents such as polyoxyethylated fats I or alcohols, alkyl alcohols, etc. Phenyl sulfonate and dispersant, such as sodium lignin sulfonate, 2.
Contains sodium 2'-(29) dinaphthylmethane-6,6'-disulfonate, sodium diptylnaphthalene sulfonate, or sodium oleylmethyltaurate. They are manufactured by customary methods, for example by grinding and mixing the components.

Emulsions can be prepared, for example, by dissolving the active substance in an inert organic solvent, such as butanol, cyclohexanone, dimethylformamide, aromatic compounds or hydrocarbons with a higher boiling point than xylene, and adding one or more emulsifiers. can be manufactured by. If the active ingredient is a liquid, all or part of the solvent portion can be omitted. As emulsifiers the following may be used, for example calcium alkylarylsulfonates such as calcium nidodecylbenzenesulfonate or non-ionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene Oxy(30)-doethylene oxide condensation products, fatty alcohol-propylene oxide-ethylene oxide condensation products, alkyl polyglycol ethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxyethylene sorbitol esters.

Powders are obtained by grinding the active substance with a finely dispersed solid substance, such as talc, or a natural clay, such as kaolin, bentonite, lacustrine or diatomite, (31) Granules. granular inert substances such as sand, kaolinite or by spraying the active substance onto adsorbent granular inert substances or by adhesives such as polyvinyl alcohol, sodium polyacrylate or mineral oil. Suitable active substances can be granulated in a manner customary for the production of fertilizer granules, if desired in a mixture with fertilizers. can.

Before hydration, the concentration of the active substance is, for example, about , about 10 to 80% by weight.
They typically contain 5 to 20% by weight of active substance, and spray solutions contain about 2 to 20% by weight. In granules, the content of active substance depends in part on whether the active substance is present as a liquid or a solid and on what granulation aids, fillers, etc. are used. Published.

Furthermore, the active substance preparations mentioned above optionally contain the customary adhesives, wetting agents, dispersants, emulsifiers, penetrants, solvents, fillers or phase substances in each case.

Concentrates that are present in commercially available form may, for use,
It is optionally diluted with water in the customary manner, for example before hydration, in emulsions, dispersions and, in some cases, microgranules. Powders and granules as well as solutions for spraying are no longer diluted with inert substances before use.

Optionally, mixtures or mixed preparations with other active substances such as biocides, acaricides, herbicides, fertilizers, plant growth regulators or fungicides are also possible. Particularly in mixtures with sterile cuttings, an enhanced synergistic effect is achieved in some cases.

The concentration used varies within a range depending on the purpose and time of use. For use as a herbicide, υ. 3 to tolc,/ha.

A suitable scale of 0.5 to 31 degrees/ha 7D 16 degrees is used.

When used as a plant growth corner 1 trimming, the concentration used is naturally lower, about 0.7 to 2 KP/ha,
Depending on the plant type, the required concentration can vary considerably.

The invention is illustrated in more detail in the following examples: A) Preparation Example 1 H Ethyl acetate 80 lnlnl medimethylphosphoxide [5°6 f (0,2 mol) in a solution of glyoxyl in ethyl acetate 80 me 14.8 P (0.2 mol) of acid solution is added dropwise. At that time, the temperature will rise somewhat. After 24 hours of keg pressing at 25°C, the product was filtered with suction, washed with a little ethyl acetate and dried, with a melting point of 206-208°C.
The desired product 20.25' (66.5 units) is obtained.

Example 2 Dimethylphosphine oxide [5] in 50 ml of CH dioxane
゜6 Add dioxane aatne to a solution of P (0.2 mol)
Medium glyoxylic acid methyl ester 17°6p (11,2
molar) ■Add the solution dropwise. 1 portion of sodium methane was added with a spatula tip, stirred for 24 hours at 25° C., the evaporated residue was freed from dioxane under high vacuum, taken up in ethyl acetate and triturated. later melting point 84~
Colorless product L6. at 86°C. (g(49,4ch) is obtained.

Example 3 2-(dimethylphosphinoyl)-2-human CH 2-(dimethylphosphinoyl-2-
A 25% aqueous ammonia solution 107 is added dropwise to a solution of 15.2 y-(11.1 mol) of hydroxy-acetic acid. At this time, the temperature increases by about 38°C. Stir for L hours at 25° C. and concentrate on a rotary evaporator. Remaining r'ff
The mixture is azeotropically dehydrated with toluene, and then boiled with tolyl. Salt with melting point 183-186°C 14.
3P C84,6ch) remains.

Example 4 11-+ (CH,), P -CiH-Coo H, N-C3H?
(n) Replacement 01 (2-(dimethylphosphinoyl)-2 in 30 ml of water!
8.97 (0.15 mol) of propylamine are added dropwise to a solution of 15.2 P (0.1 mol) of -hydroxy-acetic acid. The temperature then rises from 23°C to 38°C. 25
Wait for 1 hour at °C, stir, and concentrate on a rotary evaporator (2,
The residue is then subjected to dehydration by distillation several times with toluene. After removing toluene under high vacuum,
Sweet n T) 2 = t, a 869 A syrupy substance remains, which solidifies into a waxy state if left for a long time.

(b) Isopropylammonium salt, which is obtained as a waxy substance, can be obtained in the same manner as in the method IJi '7).

Example 5 ester (CH3)2P-OH-C! 0OCH.

0-'C0NH-CH,QC! H.

2-(dimethylphosphimele)-2-hydroxy-acetic acid methyl ester in anhydrous dioxane 5 orttl [2°5! 9-(t),t) 75 mol) To the LD solution was first added 0.29 triethylamine, then methoxymethyl isocyanate [6°6J
(0,075 mol) is added dropwise. Press for 24 hours at 25° C., remove the solvent 2 and recrystallize the residue from diisopropyl ether/ethyl acetate. Melting point tUt℃
9.6 g (98%) of the desired product are obtained.

Example 6 CH ethanol 80 nt/! 2-(dimethylphosphinoyl)-2-hydroxyacetic acid methyl ester 217 (
0゜0L26 mol)
0) 8.7 p (0,138 mol) at a temperature of 25
Add dropwise so that the temperature does not exceed ℃. Stir for 14 hours at 25°C, concentrate on a rotary evaporator, and extract f1 from the residue.
Remove the adhering solvent under high vacuum. Melting point 152-155 after soaking with diisopropyl ether
A colorless powder of 18.8 P (89.9 °C) is obtained.

Example 7 (CH3), P -CH-0ONH2OH 2-(dimethylphosphinoyl)-z-hydroxyacetic acid methyl ester 16.651' (0.1 mol) was added to methanol by blowing NH3- gas in advance for a total of 10 minutes. 7
Dissolve in 0ml. Place this in a cylinder at 250℃
After standing for 6 days at , it is filtered, concentrated and the oil pillow O residue is soaked with ethyl acetate. An amide [2.4ψ (82°2cm)] with a melting point of 155°C is obtained.

Example 8 To a solution of methanophosphinic acid monoethyl ester 54p (0.5 mol) in OHOH ethyl acetate 2 tl tl ml is added methyl glyoxylate 447 (
A solution of 0.5 mol) is added dropwise.

Boil for 24 hours at 25°C, evaporate and remove the remainder of the solvent under high vacuum. Syrup-like thing 87f!
- remains, which is heated under reflux with 1301 J ml of concentrated HC for 18 hours. evaporated, the residue is dried to the azeotrope by stripping several times with toluene and again the remainder of the solvent is removed under high vacuum. The remaining residue is left to stand for several days before crystallizing. Soaked with ethyl acetate, colorless powder 2 with melting point 53-157°C
6゜8ψ (34,8 section)? obtain.

Example 9 2-(dimethylphosphinoyl)-2-hydroxy-acetic acid methyl ester in 1 chloroform + 00 m/23.
To a solution of 4y-(0.15 mol), add chloroform 20
Medium-resistant thionyl chloride 17.9P (O,t S mol) is added dropwise under water cooling so that the temperature does not exceed 25°C. 24
After a period of time, it is evaporated and the remaining syrup is freed from adhering solvent under high vacuum. syrup-like substance 2
5 fi' (100 V) remains, which according to NHR has a purity of about 85 B and the desired composition (Continued). The powder is obtained by mixing the commercial parts and grinding in a thermos mill.

b) 25 parts a' of active substance, 64 parts of kaolin-containing quartz cylinder as inert substance, 10 parts of potassium ligninsulfonate
v parts and wet temperature - and 11 parts of sodium oleyl methyl taurate were mixed before dispersion, and pin.
Milling in a disc mill results in a hydrated shavings that can be easily dispersed in water.

C) 20 parts by weight of active substance with 6 parts by weight of alkylphenol polyglycol ether (Triton
Seams and paraffinic mineral oil (boiling range) e.g. approx. 25
By mixing 71 parts by weight (at a temperature of 5 to 377° C.) and milling in a ball mill to a fineness of less than 5 microns, a dispersion concentrate is obtained that can be readily dispersed in water.

d) 15 parts by weight of active substance, 7 parts of cyclohexane as solvent
5i! An emulsion is obtained from Jr part and 10 parts by weight of oxyethylated nonylphenol (10 moles of ethylene oxide) as an emulsifier.

C) Biological Test Examples Example I Fragments of grass weeds and broad-leaved weeds glaucoma or root violet are sown in sandy loam soil in plastic pots (9 dings of straight rods); Weeds were allowed to grow for 3-5 weeks under good growth conditions in a greenhouse. Next, the compound according to the invention is hydrated! The solution, formulated as an aqueous solution, was applied as an aqueous suspension or as a spray solution to the above-ground portion of the 416 specimen by +1 mm.

The activity of the water used at that time was equivalent to 600 to 8 oz/haK. The herbicidal activity was determined visually after dispersing for about 3 weeks under optimal growth conditions in a greenhouse.

Table 1 summarizes the results of experiments using the new compounds according to the invention. The sign of rejection was used: No low effect [=0~20chi D@呆2 = 2υ~40 person's effect 3 = 40~6υchi D effect 4: 60~80 person's effect 5 = 8 +l~too ThiO effect The values shown in Table 1 clearly demonstrate the excellent herbicidal effect of the novel compounds according to the invention against economically important harmful substances over a wide range of areas.

Abbreviations used in Table 1: (Stellarja media) AB = Oat (Avena eativa) a, i, = Effective substance Table 1 Herbicidal effect example number in post-emergence treatment method A ψ A amount Herbicidal effect 6
10 53535511
N) 5
5 4 4 4 414
[055555511LI
555555 3 10 5
5 5 5 5 54a
It) 5555552
1f1 5 5
5 5 5 54b10
5 5 5 5 5 5 Examples... An aqueous suspension f of a comparison compound having various milk yields was sprayed onto grasshoppers in the field. After 4 to 8 weeks,
Sugarcane was harvested and tested for canshotosaccharide (Planters Record).
57, 133 (1') 64)).

According to the above-mentioned method, the sugar content is measured by optical polarimetry and is expressed as "pol, can θ" D phase. This number corresponds to the percentage of sucrose in the solution, assuming that sucrose is the only substance in the sugar solution that rotates the plane of polarized light.

"pol, can θ" ■ measurement is recognized as a method for measuring the sugar content of sucrose.

The results are summarized in Table 2 below.

Ge■Omote envoy Kotsu Contains i book (po1 section canθ) kg a, j
,,/ha 4 weeks after processing 8 weeks after processing Continued from page 1 Priority claim @ October 21, 1982 ■ West Germany (D
E) [Yes] P 3238958.2@l! interloper
Helmut Bürstel, Federal Republic of Germany, Frankfurt am Main, 50 am Horatskel, 65 0 Inventor: Jenn Kokur, Federal Republic of Germany, Hofheim am Taunus am Heiligenstock 1

Claims (1)

[Claims] t General formula (in the above formula, R1 and R2 are independent of each other (Cs-C1o)-
Alkyl, 0IF8, benzyl, cyclohexyl,
means cyanoethyl, phenyl or OH; l ll A11: group -00-, -0HOH, -0HOR,, -0
HHaz'. -product 00ONR, R64f (means -crystal NHR?;
R8ke-OH, -88(a, -a□)-alkoxy, (
Cs-Oa)-cycloalkoxy, (C3-C1l
)-alkenyloxy, (C3-06)-alkynyloxy, (1) phenoxy or benzyloxy (these groups are themselves substituted with OH, halogen, CFs, (Ct-04)-alkyl or (0104)-alkoxy) '(cl-C6)-alkylthios (Cs
-Ca)-cycloalkylthio, (Cmaa)-alkenylthio, (C3-06)-alkynylthio, phenylthiomata is benzylthio (these groups are themselves halogens, CF2, (0+ a,)-alkyl is ( Of
04)-alkoxy); amino, (ctct)-alkylamino, hydroxylamino, 0(01-04)-alkylhydroxylamino, di(C1-04)-alkylamino, anilino, (Cy
-Ct. )-Phenylalkylamino, C (C7'
1G)-phenylalkylamino, N-phenyl-N
CCs '4)-alkylamino, N-722-'(Cs-Cs)-alkenylamino- or N-phenyl-"-(caaa)-alkynylamino (these groups themselves OH, halo(2) Gen, (C1-04)-alkyl or (C1-04)
- may be substituted with alkoxy); hydrazino,
β-(C1-04)-argylhydrazino, β, β-di(C1-C2)-alkylhydrazino, piperidino,
means pyrrolidino, morpholino, 2,6-dimethylmorpholino or a group represented by the formula; R4 means (CI-0s)-alkyl, allyl, bronocurgyl, benzyl or norogenbenzyl; RlI or R6 means Hydrogen, (0+ '1
2)-alkyl, (O8es)-cycloalkyl, (
Ca-Oa)-alkenyl, (C3-06)-alkynyl, phenyl, benzyl, benzoyl, phenoxysulfonyl, ('+'+2)-alkylsulfonyl,
(C1!-06)-alkenylsulfonyl or tahphenylsulfonyl (these groups are themselves), rogene, OF
3, ON, (CI-04)-(3) optionally substituted with alkoxy or (C,-C4)-alkoxycarbonyl); R1 is hydrogen, (
cl-c, )-alkyl, (c, -C6)-alkenyl, (Cs's)-alkynyl, (C8-a, )-acyl, halogen-(cl-0,)-acy/I/ or benzoyl R8 and ROFi independently of each other mean (c, -cm)-alkyl or together mean an alkylene group having 3 to 8 carbon atoms) and their bases or acids; (However, when A is a group represented by the formula %, R1 and R3 are not simultaneously -OH). 2, R1 and R6 mean methyl, A is the group CHOH
and R3 is -OH and -o-(a, -c,
Compounds according to claim 1, meaning o)-alkyl and (in the case of Rs-OH) their salts with inorganic or organic bases. 52-(Dimethylphosphinoyl)-2-human(4) p-xyacetic acid, its methyl ester and its ammonium- and (C1-C,)-alkylammonium salts. Compounds according to claim M1. 4 general formula (in the above formula, R1 and R2 are independently (c, -a,.) -alkyl, OF3, benzyl, cyclohexyl, cyanoethyl, phenyl, tROHR3 is -OH, -EIH,
(C1-01,)-alkoxy, (0++0a)-cycloalkoxy, (CI'@)-IA)rnyloxy, (
Cs-Ca)-alkynyloxy, phenoxy or benzyloxy (these groups themselves are OH, halogen,
(5) OF,,(c,-C4)-alkyl or (c,-c,
)-alkoxy): (CI-C
6)-Alkylthio, (C3-Ca)-cycloalkylthio, (csas)-alkenylthio, (csas)-
Alkynylthio, phenylthio or benzylthio (these groups are themselves halogens, OF, (01”h)-
(optionally substituted with alkyl or (C1-04)-alkoxy); amino, (C1-04)-alkylamino, hydroxylamino, 0-(CI-04)-alkylhydroxylamino, di(C1'4) -Alkylamino, Anilino, (Ov Oso)-Phenylalkylamino, C(C7-c,.)-Phenylalkylamino, N-1enyl-N(CI-04)-Alkylamino, N-phenyl-N""' (as 'a)-
Alkenylamino-strapping N-phenyl-N-(0,
-0,)-alkynylamino (these groups are themselves O
H, halogen, (0,-0゜-alkylotani(C,-
0,)-alkoxy(6)); hydrazino, β-(C1-
C4)-alkylhydrazino, β, β-G(0104
)-alkylhydrazino, piperidino, pyrrolidino, morpholino, 2,6-dimethylmorpholino or a group represented by the formula; R4 means (C1-06)-alkyl, allyl, propargyl, benzyl or halogenbenzyl; R5 and R6 are independently hydrogen, (0l-Ctt
)-alkyl, (Cs's)-cycloalkyl, (o
se@)-alkenyl, C05-Ca')-alkynyl, phenyl, benzyl, benzoyl, phenoxysulfonyl (a,C□)-alkylsulfonyl, (C3-
C.)-Alkenylsulfonyl is phenylsulfonyl (the stiff group itself is a halogen, OF, ON, (
at-number 0)-alkoxy (Ct'a)-al(
7) optionally substituted with koxycarbonyl; R7 is hydrogen, (C1-06)-alkyl, (Ctoa)
-alkenyl, (OgOs)-alkynyl, (C1-0
4) -Acyl, halogen-(0,-0,)-acyl or benzoyl; R8 and R9 independently of each other (C1-'1-alkyl or together 3 to 8 carbon means an alkylene group having an atom) and salts thereof with bases or acids (however, R and R7 are at the same time - when A is a group represented by the formula % formula %) In order to produce a compound in which A means 10=O, formula (6) (in the above formula, R, ? and R1 ke( C1-010)-A/l/near key/or has one of the meanings of R1 and R2 (excluding OH)) with the formula %Formula %() 1 (b) In order to prepare a compound in which A means 10 HOH or 10 HIJH, the formula (in which R and R: ala , .) - having the respective meanings of R1 and R2 meaning alkoxy)
A compound represented by the formula % () (9) (in the above formula, ,−”
((C1-Cs)alkyl), , -Nl(O,T(
, or -N1'1OOO(0,-0,) 7 (meaning sul), and optionally the existing group R1° is cleaved by hydrogenation w4 or hydrolysis: (C) converting the compound of formula I obtained according to (b) into another compound of formula l by alkylation, halogenation, benzylation, oxidation, acylation or amination, and optionally A method for producing a compound represented by formula I (10), which comprises hydrolyzing the alkoxy group present at the R7 position of R+t or converting the acid into its salt. (5) General formula (in the above formula, R1 and F, independently of each other, mean (C, -C,.)-alkyl, CF3, benzyl, cyclohexyl, cyanoethyl, phenyl or OH;
1 1 'R3key0H1-8) (, (C+0tt)-alkoxy, (c. -C6)-cycloalkoxy, (CsC'6)-alkenyloxy, (C3-C6)-alkynyloxy, phenoxy Benzyloxy (these groups themselves are O)
H, halogen, ay8, optionally substituted with (C,-C,)-alkyl or (01-04)-alkoxy); (Ol-06)-alkylthio, (asps)-
Cycloalkylthio, (cs,ca)-alkenylthio, (11) (Csoa)phenylthio, phenylthio, and benzylthio (these groups themselves are halogens, CF3, (0
(Optionally substituted with 1-0,)-7/l/kyl or (CI'4)-alkoxy); amino, (CI-C4
)-alkylamino, hydroxylamino, 0-(a,
-04)-alkylhydroxylamino, di(C+'
4)-alkylamino, anilino, (Cl-CIG)-
Phenylalkylamino, C(c-Cn) phenylalkylamino, N-phenyl'(C1-04,)-
Alkylamino, N-phenyl-N-(C3-oel)
-alkenylamino- or N-phenyl-N-(Cs
oa)-alkynylamino (these groups are themselves OH
, halogen, (C1-04)-alkyl or (C1'
4) -Optionally substituted with alkoxy); hydrazino, β-(C1-C,)-alkylhydrazino, β, β
-di(C1-04)-alkylhydrazino, piperidino, pyrrolidino, morpholino, 2,6-C2) dimethylmorpholinoma9 means a group represented by the formula; R4Fi(CtOa)-alkyl, allyl, propargyl, Benzyl or halogenbenzyl means: RI+ and R8 independently hydrogen, (C1-Cl
! ! )-alkyl, (Cs O,)-cycloalkyl, (csaa)-alkenyl, (csaa)-alkynyl, phenyl, benzyl, benzoyl, phenoxysulfonyl% (CI-01□)-alkylsulfonyl, (Cs's)- alkenylsulfonyl or phenylsulfonyl (these 1 groups are themselves halogen, CF,
, ON, (0°-No. 0)-alkoxy make (0104
)-alkoxycarbonyl); R is hydrogen, (C1-C0)-alkyl, (Ct'a)
-alkenyl, (csas)-alkynyl, (13) (c, -c number)-acyl, halogen-(C1-04)-
acyl or benzoyl; R8 and R9 independently of each other mean (c+'+t)-alkyl or together mean an alkylene group having 3 to 8 carbon atoms) and their A herbicide and plant growth agent characterized by containing a salt with a base or an acid (however, when R8 and R2 are groups represented by the formula %, they are not simultaneously -OH) Conditioner. 6. The agent according to claim 5, which is used for controlling undesirable plant growth and/or increasing the content of desirable plant contents.