IL35850A - Phosphorus containing amidine compounds,their preparation and their use as insecticides and acaricides - Google Patents

Phosphorus containing amidine compounds,their preparation and their use as insecticides and acaricides

Info

Publication number: IL35850A
Authority: IL; Israel
Prior art keywords: carbon atoms; methyl; methoxy; methylthio; compound
Prior art date: 1969-12-15

Application number

IL35850A

Other languages

English (en)

Other versions

IL35850A0 (en

Original Assignee

Stauffer Chemical Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1969-12-15

Filing date

1970-12-14

Publication date

1973-06-29

1970-12-14 Application filed by Stauffer Chemical Co filed Critical Stauffer Chemical Co

1971-02-25 Publication of IL35850A0 publication Critical patent/IL35850A0/xx

1973-06-29 Publication of IL35850A publication Critical patent/IL35850A/en

Links

-1 amidine compounds Chemical class 0.000 title claims description 13
239000002917 insecticide Substances 0.000 title description 5
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title description 4
229910052698 phosphorus Inorganic materials 0.000 title description 4
239000011574 phosphorus Substances 0.000 title description 4
230000000895 acaricidal effect Effects 0.000 title description 3
239000000642 acaricide Substances 0.000 title description 3
238000002360 preparation method Methods 0.000 title description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 48
150000001875 compounds Chemical class 0.000 claims description 35
238000000034 method Methods 0.000 claims description 30
125000000217 alkyl group Chemical group 0.000 claims description 29
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
125000003545 alkoxy group Chemical group 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 12
125000004414 alkyl thio group Chemical group 0.000 claims description 9
241000238631 Hexapoda Species 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
150000002431 hydrogen Chemical group 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
239000011593 sulfur Substances 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 18
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 17
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 12
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
125000004429 atom Chemical group 0.000 claims 2
238000004519 manufacturing process Methods 0.000 claims 1
125000001424 substituent group Chemical group 0.000 claims 1
241001425390 Aphis fabae Species 0.000 description 13
241000196324 Embryophyta Species 0.000 description 13
231100000167 toxic agent Toxicity 0.000 description 12
239000003440 toxic substance Substances 0.000 description 12
RXKUYBRRTKRGME-UHFFFAOYSA-N butanimidamide Chemical compound CCCC(N)=N RXKUYBRRTKRGME-UHFFFAOYSA-N 0.000 description 11
241000258913 Oncopeltus fasciatus Species 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
241001414823 Lygus hesperus Species 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
241000257159 Musca domestica Species 0.000 description 7
239000002904 solvent Substances 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
238000011156 evaluation Methods 0.000 description 6
239000000243 solution Substances 0.000 description 6
241001454293 Tetranychus urticae Species 0.000 description 5
239000000203 mixture Substances 0.000 description 5
239000002689 soil Substances 0.000 description 5
244000046052 Phaseolus vulgaris Species 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
239000006185 dispersion Substances 0.000 description 4
230000000749 insecticidal effect Effects 0.000 description 4
239000007787 solid Substances 0.000 description 4
230000009885 systemic effect Effects 0.000 description 4
STECJAGHUSJQJN-USLFZFAMSA-N LSM-4015 Chemical compound C1([C@@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-USLFZFAMSA-N 0.000 description 3
241000208241 Tropaeolum Species 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
239000004744 fabric Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
230000000361 pesticidal effect Effects 0.000 description 3
125000005499 phosphonyl group Chemical group 0.000 description 3
239000000376 reactant Substances 0.000 description 3
239000007921 spray Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000012085 test solution Substances 0.000 description 3
241001124076 Aphididae Species 0.000 description 2
229920000298 Cellophane Polymers 0.000 description 2
229920000742 Cotton Polymers 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
241000894007 species Species 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 1
241000238876 Acari Species 0.000 description 1
244000045232 Canavalia ensiformis Species 0.000 description 1
241000255925 Diptera Species 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
241000219146 Gossypium Species 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
240000007049 Juglans regia Species 0.000 description 1
235000009496 Juglans regia Nutrition 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
241000257226 Muscidae Species 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
241000219833 Phaseolus Species 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 1
241000209140 Triticum Species 0.000 description 1
235000021307 Triticum Nutrition 0.000 description 1
235000004424 Tropaeolum majus Nutrition 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
150000001409 amidines Chemical class 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 1
239000003599 detergent Substances 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
238000007865 diluting Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
239000000295 fuel oil Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
150000002790 naphthalenes Chemical class 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
229920000151 polyglycol Polymers 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
229940051841 polyoxyethylene ether Drugs 0.000 description 1
229920000056 polyoxyethylene ether Polymers 0.000 description 1
229940096992 potassium oleate Drugs 0.000 description 1
MLICVSDCCDDWMD-KVVVOXFISA-M potassium;(z)-octadec-9-enoate Chemical compound [K+].CCCCCCCC\C=C/CCCCCCCC([O-])=O MLICVSDCCDDWMD-KVVVOXFISA-M 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000000344 soap Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
239000012265 solid product Substances 0.000 description 1
229940035044 sorbitan monolaurate Drugs 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
230000005945 translocation Effects 0.000 description 1
235000020234 walnut Nutrition 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2458—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic of aliphatic amines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/44—Amides thereof
- C07F9/4461—Amides thereof the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4465—Amides thereof the amide moiety containing a substituent or a structure which is considered as characteristic of aliphatic amines

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

IL35850A 1969-12-15 1970-12-14 Phosphorus containing amidine compounds,their preparation and their use as insecticides and acaricides IL35850A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US88526369A	1969-12-15	1969-12-15

Publications (2)

Publication Number	Publication Date
IL35850A0 IL35850A0 (en)	1971-02-25
IL35850A true IL35850A (en)	1973-06-29

Family

ID=25386508

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL35850A IL35850A (en)	1969-12-15	1970-12-14	Phosphorus containing amidine compounds,their preparation and their use as insecticides and acaricides

Country Status (11)

Country	Link
US (1)	US3734980A (es)
JP (1)	JPS541776B1 (es)
BE (1)	BE760287A (es)
CA (1)	CA921483A (es)
CH (1)	CH540646A (es)
DE (1)	DE2061058A1 (es)
ES (1)	ES403798A1 (es)
FR (1)	FR2073668A5 (es)
GB (1)	GB1302249A (es)
IL (1)	IL35850A (es)
NL (1)	NL7018209A (es)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3975522A (en)	1971-12-17	1976-08-17	Ciba-Geigy Corporation	Control of insects and acarids with N-phosphinylamidines
US3925517A (en) *	1973-11-05	1975-12-09	Ciba Geigy Corp	Phosphorylformamidines
DE2737403A1 (de) *	1977-08-19	1979-02-22	Bayer Ag	N-(aminomethylen)-(mono- bzw. dithio) -phosphorsaeurediesteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematizide

1969
- 1969-12-15 US US00885263A patent/US3734980A/en not_active Expired - Lifetime
1970
- 1970-09-01 GB GB4171770A patent/GB1302249A/en not_active Expired
- 1970-10-16 CA CA095760A patent/CA921483A/en not_active Expired
- 1970-12-10 CH CH1842970A patent/CH540646A/de not_active IP Right Cessation
- 1970-12-11 FR FR7044829A patent/FR2073668A5/fr not_active Expired
- 1970-12-11 DE DE19702061058 patent/DE2061058A1/de active Pending
- 1970-12-14 JP JP11108770A patent/JPS541776B1/ja active Pending
- 1970-12-14 NL NL7018209A patent/NL7018209A/xx unknown
- 1970-12-14 IL IL35850A patent/IL35850A/en unknown
- 1970-12-14 BE BE760287A patent/BE760287A/xx unknown
1972
- 1972-06-13 ES ES403798A patent/ES403798A1/es not_active Expired

Also Published As

Publication number	Publication date
NL7018209A (es)	1971-06-17
IL35850A0 (en)	1971-02-25
FR2073668A5 (es)	1971-10-01
CA921483A (en)	1973-02-20
ES403798A1 (es)	1975-05-01
CH540646A (de)	1973-08-31
US3734980A (en)	1973-05-22
DE2061058A1 (de)	1971-06-16
JPS541776B1 (es)	1979-01-29
GB1302249A (es)	1973-01-04
BE760287A (fr)	1971-06-14

Publication	Publication Date	Title
US3591600A (en)	1971-07-06	2-aminothiazole phosphates and phosphonates
US3725514A (en)	1973-04-03	O-aryl o-alkyl s-organo phosphorothidates
US3825632A (en)	1974-07-23	Phosphorus-containing amidines
US3826830A (en)	1974-07-30	Certain phosphorus containing amidine compounds as insecticides and acaricides
US3518327A (en)	1970-06-30	Phosphoro and phosphono acetylhydrazides
IL35850A (en)	1973-06-29	Phosphorus containing amidine compounds,their preparation and their use as insecticides and acaricides
US3749775A (en)	1973-07-31	Insecticidal 2-aminothiazole phosphates and phosphonates
US3758685A (en)	1973-09-11	Caricides certain phosphorus containing amidine compounds as insecticides and a
US3810959A (en)	1974-05-14	N-(alkoxyalyl)-o-alkyl-s-alkylthio-phosphors-amides
US3897516A (en)	1975-07-29	Oximino phosphorus compounds
US3636206A (en)	1972-01-18	Certain thiolophosphonamides as insecticides and acaricides
US3723450A (en)	1973-03-27	Phosphonamido thiazoles and their utility as insecticides
US4137308A (en)	1979-01-30	1,3-Oxazole phosphates and phosphonates as insecticides and miticides
US3660541A (en)	1972-05-02	Oximino phosphates and phosphonates
US3760040A (en)	1973-09-18	Phosphorus containing compounds
US3737530A (en)	1973-06-05	Certain oximinophosphonodithioates as insecticides and acaricides
US3978106A (en)	1976-08-31	Certain thioformaldoximino dithiophosphoric acids
US3652736A (en)	1972-03-28	Oximinophosphonodithioates
US3703532A (en)	1972-11-21	Phosphorus containing coumarins
US3737528A (en)	1973-06-05	Certain oximino phosphorus containing compounds used as insecticides and acaricides
US3631170A (en)	1971-12-28	Certain oximino phosphorus containing pyrimidines
US3769375A (en)	1973-10-30	Oximino phosphorus compounds
US4016266A (en)	1977-04-05	N-Alkylthiomethylacetamidephosphorodithioate insecticides
US3709959A (en)	1973-01-09	Oximinophosphonodithioates
US3364230A (en)	1968-01-16	Novel phosphorylated 2-imino-1, 3-dithioles